Flavor composition containing HMG glucosides

ABSTRACT

A flavor composition containing at least one HMG glucoside compound that can be used to enhance the taste of edible compositions including sweet goods, such as confectionery goods, and savory goods, such as pet foods.

CROSS-REFERENCE TO RELATED APPLICATION

The present application is a continuation of U.S. patent applicationSer. No. 16/542,665, filed on Aug. 16, 2019, which is a divisional ofU.S. patent application Ser. No. 14/772,682, filed on Sep. 3, 2015, nowU.S. Pat. No. 10,414,787, which is a U.S. National Stage PatentApplication under 35 U.S.C. § 371 of International Application No.PCT/US2014/023727, filed on Mar. 11, 2014, which claims priority to U.S.Provisional Application Serial No. 61/785,702, filed on Mar. 14, 2013,the contents of each of which is are incorporated by reference in itstheir entirety herein.

FIELD

The present application relates to HMG glucosides and flavorcompositions that include at least one HMG glucoside compound. Theflavor compositions can be used to enhance or modify the taste and/orflavor of various edible compositions such as sweet goods and savorygoods. The flavor compositions can include combinations of compounds,and can be added to edible compositions in various delivery systemformats.

BACKGROUND

Taste profiles for edible compositions include basic tastes such assweet, salt, bitter, sour, umami and kokumi. Chemical compounds thatelicit these tastes are often referred to as tastants. It ishypothesized that tastants are sensed by taste receptors in the mouthand throat which transmit signals to the brain where the tastants andresulting taste profiles are registered. In addition to taste profiles,edible compositions are also known to have flavor profiles. Chemicalcompounds that contribute to flavor profiles can be aromatic compoundsthat are often referred to as flavorants. It is hypothesized thatflavorants are sensed by receptors in the mouth, nose, and throat. Takentogether, the taste and flavor profiles resulting from the varioustastants and flavorants contribute to the sensory experience users havewhen consuming the edible compositions. The sensory experience can alsoinclude various texture and temperature/thermal aspects.

While there have been recent advances in taste and flavor technologies,there remains a need for compounds that can enhance or modify thesensory experience of edible compositions by enhancing or modifying thetaste, texture, and/or flavor profiles of edible compositions. Theenhancement or modification can be to increase the intensity of adesirable attribute, to replace a desirable attribute that is notpresent or somehow lost in the edible composition, or to decrease theintensity of an undesirable attribute. It is further desirable to beable to use tastants to enhance or modify the texture of an ediblecomposition.

Vegetable proteins, such as wheat and soy, can be hydrolyzed to producehydrolysates that can be used as flavor enhancers (i.e. soy sauce). InEP1312268A1 to Nestle, wheat protein forms the starting material that ishydrolyzed to form pyroglutamic acid tripeptides that provide umamitaste. Umami taste is known to produce organoleptic affects includingproviding mouthfeel and roundness. Umami taste effect is usuallydescribed in comparison to the taste provided by monosodium glutamate(MSG). Taking a purely synthetic approach to umami compounds, U.S. Pat.No. 5,780,090 to Firmenich describes tripeptides with a hydrophobicamino acid residue and at least one acidic amino acid residue. Thesetripeptides provide fuller, richer texture (i.e. an umami effect).However, neither of these publications describe compounds that canmodify other taste, flavor and/or texture sensations. Thus, thereremains a need for a flavor modifier that can modify other taste, flavorand/or texture sensations.

SUMMARY OF THE INVENTION

The present application is directed to flavor compositions and methodsfor making and modifying such compositions across a variety of foodcompositions. Specifically, the present application is directed tocompositions comprising one or more 3-hydroxy-3-methylglutaric acid(HMG) glucosides.

In certain embodiments, the flavor compositions of the presentapplication comprise an HMG glucoside comprising the followingstructure, Formula I.

wherein R is described herein below. The present application alsoprovides salts and esters of the compounds of Formula I.

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula II):

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula III):

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula IV):

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula V):

In certain embodiments, the compounds of the application comprisestereoisomers of Formula I.

In certain embodiments, the present application provides methods ofmodifying the taste and/or flavor and/or texture of a food product,which comprise providing a flavor composition, for example, an HMGglucoside compound such as, but not limited to, an HMG glucoside ofFormula I, or combinations thereof, and admixing the flavor compositionwith a food product.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product in an amount effective toprovide a mouth watering and/or lubricating and/or slippery mouthfeel.In certain embodiments, the flavor composition is admixed with a foodproduct in an amount effective to increase or decrease a mouth wateringand/or lubricating and/or slippery mouthfeel present in the foodproduct.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product in an amount effective toprovide an astringent mouthfeel. In certain embodiments, the flavorcomposition is admixed with a food product in an amount effective toincrease or decrease an astringent mouthfeel present in the foodproduct.

In certain embodiments, the flavor composition is admixed with a foodproduct at a concentration of from about 0.1 to about 5000 ppm(parts-per-million). In certain embodiments, the flavor composition isadmixed with a food product at a concentration of from about 0.1 toabout 500 ppm. In certain embodiments, the flavor composition is admixedwith a food product at a concentration of from about 0.1 to about 100ppm. In certain embodiments, the flavor composition is admixed with afood product at a concentration of from about 0.1 to about 50 ppm.

In certain embodiments, the flavor composition is admixed with a foodproduct at a concentration of about 100 ppm.

In certain embodiments, the flavor composition is admixed with a foodproduct at a concentration of from about 0.1 to about 100 ppb(parts-per-billion). In certain embodiments, the flavor composition isadmixed with a food product at a concentration of from about 0.1 toabout 50 ppb. In certain embodiments, the flavor composition is admixedwith a food product at a concentration of from about 0.1 to about 10ppb.

In certain embodiments, the flavor composition is admixed with a foodproduct at a concentration of from about 0.0001 to about 99.9%weight/weight (w/w). In certain embodiments, the flavor composition isadmixed with a food product at a concentration of from about 0.0001 toabout 1.0% w/w. In certain embodiments, the flavor composition isadmixed with a food product at a concentration of from about 0.0001 toabout 0.5% w/w.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product in an amount effective tomodulate, enhance or decrease the taste profile of an ediblecomposition.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product in an amount effective tomodulate, enhance or decrease the flavor profile of an ediblecomposition.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product in an amount effective tomodulate, enhance or decrease the texture profile of an ediblecomposition.

In certain embodiments, the present application provides methods ofpreparing a flavor composition. In certain embodiments, the methodscomprise hydrolyzing a food product source, for example, cacao, wheat orsoy, to produce a hydrolysate comprising the flavor composition. Incertain embodiments, the hydrolysate is admixed with a food product.

In certain embodiments the flavor compositions of the presentapplication are prepared from a food product source that is fractionatedand/or extracted to form an enriched HMG glucoside compositioncomprising the HMG glucosides of the present application.

In certain embodiments the flavor compositions of the presentapplication are prepared from a food product source that is hydrolyzedand fractionated and/or extracted to form an enriched HMG glucosidecomposition comprising the HMG glucosides of the present application.

In certain embodiments, the methods of preparing a flavor compositioncomprises synthesizing an HMG glucoside flavor composition such as, butnot limited to, an HMG glucoside of Formula I, or combinations thereof.In certain embodiments, the synthesis methods are synthetic synthesismethods.

The foregoing has outlined rather broadly the features and technicaladvantages of the present application in order that the detaileddescription that follows may be better understood. Additional featuresand advantages of the application will be described hereinafter whichform the subject of the claims of the application. It should beappreciated by those skilled in the art that the conception and specificembodiment disclosed may be readily utilized as a basis for modifying ordesigning other structures for carrying out the same purposes of thepresent application. It should also be realized by those skilled in theart that such equivalent constructions do not depart from the spirit andscope of the application as set forth in the appended claims. The novelfeatures which are believed to be characteristic of the application,both as to its organization and method of operation, together withfurther objects and advantages will be better understood from thefollowing description.

BRIEF DESCRIPTION OF THE DRAWINGS

FIG. 1 shows an NMR spectrum for an isomer of Formula II synthesizedaccording to synthesis scheme 1, as described by Example 2.

FIG. 2 shows an NMR spectrum for an isomer of Formula II synthesizedaccording to synthesis scheme 2, as described by Example 2.

DETAILED DESCRIPTION

To date, there remains a need for a flavor modifier that can provide adesired level of mouth watering and/or lubricating and/or slipperyand/or astringent mouthfeel in various edible compositions. The presentapplication relates to flavor compositions that include at least one HMGglucoside compound. In certain non-limiting embodiments, the HMGglucoside comprises a compound of Formula I. The flavor compositions canbe used to enhance or modify the taste and/or flavor and/or texture ofvarious edible compositions such as sweet goods and savory goods. Theflavor compositions can include combinations of compounds, and can beadded to edible compositions in various delivery system formats.

1. Definitions

The terms used in this specification generally have their ordinarymeanings in the art, within the context of this invention and in thespecific context where each term is used. Certain terms are discussedbelow, or elsewhere in the specification, to provide additional guidanceto the practitioner in describing the compositions and methods of theinvention and how to make and use them.

As used herein, the use of the word “a” or “an” when used in conjunctionwith the term “comprising” in the claims and/or the specification maymean “one,” but it is also consistent with the meaning of “one or more,”“at least one,” and “one or more than one.” Still further, the terms“having,” “including,” “containing” and “comprising” are interchangeableand one of skill in the art is cognizant that these terms are open endedterms.

The term “about” or “approximately” means within an acceptable errorrange for the particular value as determined by one of ordinary skill inthe art, which will depend in part on how the value is measured ordetermined, i.e., the limitations of the measurement system. Forexample, “about” can mean within 3 or more than 3 standard deviations,per the practice in the art. Alternatively, “about” can mean a range ofup to 20%, preferably up to 10%, more preferably up to 5%, and morepreferably still up to 1% of a given value. Alternatively, particularlywith respect to biological systems or processes, the term can meanwithin an order of magnitude, preferably within 5-fold, and morepreferably within 2-fold, of a value.

As used herein, “taste” refers to a sensation caused by activation orinhibition of receptor cells in a subject's taste buds. In certainembodiments, taste can be selected from the group consisting of sweet,sour, salt, bitter, kokumi and umami. In certain embodiments, a taste iselicited in a subject by a “tastant.” In certain embodiments, a tastantis a synthetic tastant. In certain embodiments, the tastant is preparedfrom a natural source.

As used herein, “taste profile” refers to a combination of tastes, suchas, for example, one or more of a sweet, sour, salt, bitter, kokumiand/or umami taste. In certain embodiments, a taste profile is producedby one or more tastant that is present in a composition at the same ordifferent concentrations. In certain embodiments, a taste profile refersto the intensity of a taste or combination of tastes, for example, asweet, sour, salt, bitter, kokumi and/or umami taste, as detected by asubject or any assay known in the art. In certain embodiments,modifying, changing or varying the combination of tastants in a tasteprofile can change the sensory experience of a subject.

As used herein, “flavor” refers to one or more sensory stimuli, such as,for example, one or more of taste (gustatory), smell (olfactory), touch(tactile) and temperature (thermal) stimuli. The terms “flavor” and“aroma” are synonymous and are used interchangeably. In certainnon-limiting embodiments, the sensory experience of a subject exposed toa flavor can be classified as a characteristic experience for theparticular flavor. For example, a flavor can be identified by thesubject as being, but not limited to, a floral, citrus, berry, nutty,caramel, chocolate, peppery, smoky, cheesy, meaty, etc. flavor As usedherein, a flavor composition can be selected from a liquid, dry powder,spray, paste, suspension and any combination thereof. The flavor can bea natural composition, an artificial composition, a nature identical, orany combination thereof.

As used herein, “flavor profile” refers to a combination of sensorystimuli, for example, tastes, such as sweet, sour, bitter, salty, kokumiand/or umami tastes, and/or olfactory, tactile and/or thermal stimuli.In certain embodiments, the flavor profile comprises one or more flavorswhich contribute to the sensory experience of a subject. In certainembodiments, modifying, changing or varying the combination of stimuliin a flavor profile can change the sensory experience of a subject.

As used herein, “texture profile” or “mouthfeel” refers to acomposition's physical and chemical interaction in the mouth. Thetexture profile of a composition can include one or more texture, suchas, for example, but not limited to, mouth watering, lubricating,slippery, astringency, hardness, cohesiveness, viscosity, elasticity,adhesiveness, brittleness, chewiness, gumminess, moisture content,grittiness, smoothness, oiliness and greasiness. In certain embodiments,the texture profile can comprise one or more texture characteristic inthe same or different intensities. In certain embodiments, the textureprofile can remain constant or change during a sensory experience, forexample, from initial perception of a composition on the palate, tofirst bite, through mastication and finally, the act of swallowing.

As used herein, “sensory experience” refers to a subject's sensoryperception of a taste, taste profile, flavor, flavor profile or textureprofile.

As used herein, “ppb” means parts-per-billion and is a weight relativeparameter. A part-per-billion is a nanogram per gram, such that acomponent that is present at 10 ppb is present at 10 nanograms of thespecific component per 1 gram of the aggregate mixture.

As used herein, “ppm” means parts-per-million and is a weight relativeparameter. A part-per-million is a microgram per gram, such that acomponent that is present at 10 ppm is present at 10 micrograms of thespecific component per 1 gram of the aggregate mixture.

As used herein “admixing,” for example, “admixing the HMG glucosideflavor composition, or combinations thereof, of the present applicationwith a food product,” refers to the process where the flavor compositionis mixed with or added to the completed product or mixed with some orall of the components of the product during product formation or somecombination of these steps. When used in the context of admixing theterm “product” refers to the product or any of its components. Thisadmixing step can include a process selected from the step of adding theflavor composition to the product, spraying the flavor composition onthe product, coating the flavor composition on the product, suspendingthe product in the flavor composition, painting the flavor compositionon the product, pasting the flavor composition on the product,encapsulating the product with the flavor composition, mixing the flavorcomposition with the product and any combination thereof. The flavorcomposition can be a liquid, dry powder, spray, paste, suspension andany combination thereof.

As used herein “food product” refers to an ingestible product, such as,but not limited to, human food, animal (pet) foods, and pharmaceuticalcompositions.

As used herein “flavor composition” refers to at least one compound orbiologically acceptable salt thereof that modulates, includingenhancing, multiplying, potentiating, decreasing, suppressing, orinducing, the tastes, smells, flavors and/or textures of a natural orsynthetic tastant, flavoring agent, taste profile, flavor profile and/ortexture profile in an animal or a human. In certain embodiments, theflavor composition comprises a combination of compounds or biologicallyacceptable salts thereof. In certain embodiments, the flavor compositionincludes one or more excipients.

As used herein “savory flavor” refers to a savory, “mouth-watering,”sensation. In certain embodiments, a savory flavor is induced by one ormore combination of umami tastants, for example, MSG (monosodiumglutamate) in an animal or a human.

In certain embodiments, “wet soup category” means wet/liquid soupsregardless of concentration or container, including frozen soups. Forthe purpose of this definition “soup(s)” means a food prepared frommeat, poultry, fish, vegetables, grains, fruit and/or other ingredients,cooked in a liquid which may include visible pieces of some or all ofthese ingredients. It may be clear (as a broth) or thick (as a chowder),smooth, pureed or chunky, ready-to-serve, semi-condensed or condensedand may be served hot or cold, as a first course or as the main courseof a meal or as a between meal snack (sipped like a beverage). Soup maybe used as an ingredient for preparing other meal components and mayrange from broths (consomme) to sauces (cream or cheese-based soups).

As used herein, “dehydrated and culinary food category” means: (i)Cooking aid products such as: powders, granules, pastes, concentratedliquid products, including concentrated bouillon, bouillon and bouillonlike products in pressed cubes, tablets or powder or granulated form,which are sold separately as a finished product or as an ingredientwithin a product, sauces and recipe mixes (regardless of technology);(ii) Meal solution products such as: dehydrated and freeze dried soups,including dehydrated soup mixes, dehydrated instant soups, dehydratedready-to-cook soups, dehydrated or ambient preparations of ready-madedishes, meals and single serve entrees including pasta, potato and ricedishes; and (iii) Meal embellishment products such as: condiments,marinades, salad dressings, salad toppings, dips, breading, battermixes, shelf stable spreads, barbecue sauces, liquid recipe mixes,concentrates, sauces or sauce mixes, including recipe mixes for salad,sold as a finished product or as an ingredient within a product, whetherdehydrated, liquid or frozen.

As used herein, “beverage category” means beverages, beverage mixes andconcentrates, including but not limited to, alcoholic and non-alcoholicready to drink and dry powdered beverages. Other examples of foods andbeverages wherein compounds according to the application may beincorporated included by way of example carbonated and non-carbonatedbeverages, e.g., sodas, fruit or vegetable juices, alcoholic andnon-alcoholic beverages, confectionary products, e.g., salad dressings,and other condiments, cereal, and other breakfast foods, canned fruitsand fruit sauces and the like.

As used herein, “frozen food category” means chilled or frozen foodproducts. Non-limiting examples of food products of the frozen foodcategory include ice cream, impulse ice cream, single portion dairy icecream, single portion water ice cream, multi-pack dairy ice cream,multi-pack water ice cream, take-home ice cream, take-home dairy icecream, ice cream desserts, bulk ice cream, take-home water ice cream,frozen yoghurt, artisanal ice cream, frozen ready meals, frozen pizza,chilled pizza, frozen soup, frozen pasta, frozen processed red meat,frozen processed poultry, frozen processed fish/seafood, frozenvegetables, frozen processed vegetables, frozen meat substitutes, frozenpotatoes, frozen bakery products and frozen desserts.

As used herein, “snack food category” generally refers to any food thatcan be a light informal meal including, but not limited to sweet andsavory snacks and snack bars. Examples of snack foods include, but arenot limited to, fruit snacks, chips/crisps, extruded snacks,tortilla/corn chips, popcorn, pretzels, nuts and other sweet and savorysnacks. Examples of snack bars include, but are not limited togranola/muesli bars, breakfast bars, energy bars, fruit bars and othersnack bars.

As used herein, “meat food product” refers generally to a food productmade by processing the edible remains of any dead animal, includingbirds, fish, crustaceans, shellfish and mammals. Meat food productsinclude, without limitation, for example, prepared beef, lamb, pork,poultry or seafood products. For example, meat food products includebologna, frankfurters, sausage, luncheon, deli slices, loaves, bacon,meatballs, fish sticks, chicken fingers, and ground meats, e.g.,meatloaf, meatballs and hamburgers.

As used herein, “simulated meat food product” includes, withoutlimitation, for example, a meat alternative, meat analog, soy burger,soy bologna, soy frankfurter, soy sausage, soy luncheon loaves, soybacon and soy meatball.

As used herein, “food product source” refers generally to the rawproducts from which a food product is made. In certain embodiments, thefood product source is a vegetable, fruit or any other plant material.In certain embodiments, the plant material is cacao, cocoa beans, orcocoa liquor. In other embodiments, the food product source comprisesthe remains of any dead animal, including birds, fish, crustaceans,shellfish and mammals.

The term “alkyl” refers to a straight or branched C₁-C₂₀ (preferablyC₁-C₆) hydrocarbon group consisting solely of carbon and hydrogen atoms,containing no unsaturation, and which is attached to the rest of themolecule by a single bond, e.g., methyl, ethyl, n-propyl, 1-methylethyl(isopropyl), n-butyl, n-pentyl, 1,1-dimethylethyl (t-butyl).

The term “alkenyl” refers to a C₂-C₂₀ (preferably C₁-C₄) aliphatichydrocarbon group containing at least one carbon-carbon double bond andwhich may be a straight or branched chain, e.g., ethenyl, 1-propenyl,2-propenyl (allyl), iso-propenyl, 2-methyl-1-propenyl, 1-butenyl,2-butenyl.

The term “cycloalkyl” denotes an unsaturated, non-aromatic mono- ormulticyclic hydrocarbon ring system (containing, for example, C₃-C₆)such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl. Examples ofmulticyclic cycloalkyl groups (containing, for example, C₆-C₁₅) includeperhydronapththyl, adamantyl and norbornyl groups bridged cyclic groupor sprirobicyclic groups, e.g., spiro (4,4) non-2-yl.

The term “cycloalkalkyl” refers to a cycloalkyl as defined abovedirectly attached to an alkyl group as defined above, that results inthe creation of a stable structure such as cyclopropylmethyl,cyclobutylethyl, cyclopentylethyl.

The term “alkyl ether” refers to an alkyl group or cycloalkyl group asdefined above having at least one oxygen incorporated into the alkylchain, e.g., methyl ethyl ether, diethyl ether, tetrahydrofuran.

The term “alkyl amine” refers to an alkyl group or a cycloalkyl group asdefined above having at least one nitrogen atom, e.g., n-butyl amine andtetrahydrooxazine.

The term “aryl” refers to aromatic radicals having in the range of about6 to about 14 carbon atoms such as phenyl, naphthyl, tetrahydronapthyl,indanyl, biphenyl.

The term “arylalkyl” refers to an aryl group as defined above directlybonded to an alkyl group as defined above, e.g., —CH₂C₆H₅, and—C₂H₄C₆H₅.

The term “heterocyclic” refers to a stable 3- to 15-membered ringradical which consists of carbon atoms and one or more, for example,from one to five, heteroatoms selected from the group consisting ofnitrogen, oxygen and sulfur. For purposes of this application, theheterocyclic ring radical may be a monocyclic or bicyclic ring system,which may include fused or bridged ring systems, and the nitrogen,carbon, oxygen or sulfur atoms in the heterocyclic ring radical may beoptionally oxidized to various oxidation states. In addition, thenitrogen atom may be optionally quaternized; and the ring radical may bepartially or fully saturated (i.e., heteroaromatic or heteroarylaromatic).

The heterocyclic ring radical may be attached to the main structure atany heteroatom or carbon atom that results in the creation of a stablestructure.

The term “heteroaryl” refers to a heterocyclic ring wherein the ring isaromatic.

The term “heteroarylalkyl” refers to heteroaryl ring radical as definedabove directly bonded to alkyl group. The heteroarylalkyl radical may beattached to the main structure at any carbon atom from alkyl group thatresults in the creation of a stable structure.

The term “heterocyclyl” refers to a heterocylic ring radical as definedabove. The heterocyclyl ring radical may be attached to the mainstructure at any heteroatom or carbon atom that results in the creationof a stable structure.

2. HMG Glucoside Compounds

The present application relates to flavor compositions that include atleast one 3-hydroxy-3-methylglutaric acid (HMG) glucoside compound (HMGglucoside). The flavor compositions can be used to enhance or modify thetaste and/or flavor and/or texture of various edible compositions suchas sweet goods and savory goods. The flavor compositions can includecombinations of compounds, and can be added to edible compositions invarious delivery system formats.

In certain non-limiting embodiments, the HMG glucoside comprises acompound of Formula I having the following structure.

wherein R is selected from the group consisting of substituted orunsubstituted alkyl, substituted or unsubstituted alkenyl, substitutedor unsubstituted cycloalkyl, substituted or unsubstituted aryl,substituted or unsubstituted cycloalkalkyl, substituted or unsubstitutedarylalkyl, substituted or unsubstituted heteroarylalkyl, substituted orunsubstituted heteroaryl, substituted or unsubstituted heterocyclic,substituted or unsubstituted alkoxy, substituted or unsubstitutedaryloxy, hydroxyl, hydrogen, substituted or unsubstituted ether,substituted or unsubstituted benzothiazol, substituted or unsubstitutedpyridyl, substituted or unsubstituted naphthyl, substituted orunsubstituted phenyl, substituted or unsubstituted thienyl, substitutedor unsubstituted benzothienyl, substituted or unsubstituted indol,substituted or unsubstituted isoquinolyl, substituted or unsubstitutedquinolyl, —C(O)R¹ and —S(O)₂R¹, wherein R¹ is defined as above for R.

The substituents in the substituted groups described herein, forexample, “substituted ether”, “substituted alkyl”, “substitutedalkenyl”, “substituted cycloalkyl”, “substituted cycloalkalkyl”,“substituted arylalkyl”, “substituted aryl”, “substituted heterocyclic”,“substituted heteroarylalkyl,” “substituted heteroaryl”, “substitutednaphthyl”, “substituted phenyl”, “substituted thienyl”, “substitutedbenzothienyl”, “substituted pyridyl”, “substituted indol”, “substitutedisoquinolyl”, “substituted quinolyl”, or “substituted benzothiazol” maybe the same or different with one or more selected from the groupsdescribed in the present application and hydrogen, halogen, amide,acetyl, nitro, oxo (═O), thio (═S), —NO₂, —CF₃, —OCH₃, -Boc oroptionally substituted groups selected from alkyl, alkoxy, aryl,aryloxy, arylalkyl, ether, ester, hydroxyl, heteroaryl, and heterocyclicring. A “substituted” functionality may have one or more than onesubstituent.

In one non-limiting embodiment, R is isopentyl, or an isopentylderivative.

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula II):

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula III):

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula IV):

In certain embodiments, the compounds of the application comprise thefollowing structure (Formula V):

In certain embodiments, the compounds of the application comprisestereoisomers of Formula I.

In certain embodiments, the compounds of the application comprise astereoisomer of Formula II, comprising a structure selected from thegroup consisting of:

and combinations thereof.

In certain embodiments, the HMG glucoside compounds of the presentapplication comprise a salt of the HMG glucoside, for example, but notlimited to, an acetate salt, a TFA salt, or a formate salt. In certainembodiments, the HMG glucoside salt comprises an anion (−) (for example,but not limited to, Cl⁻, F⁻, Br, O²⁻, CO₃ ²⁻, HCO₃ ⁻, OH⁻, NO₃ ⁻, PO₄³⁻, SO₄ ²⁻, CH₃COO⁻, HCOO⁻, C₂O₄ ²⁻ and CN) bonded via an ionic bondwith a cation (+) (for example, but not limited to, Al³⁺, Ca²⁺, Na⁺, K⁺,Cu²⁺, H⁺, Fe³⁺, Mg²⁺, Ag⁺, NH₄ ⁺, H₃O⁺, Hg₂ ²⁺). In other embodiments,the HMG glucoside salt comprises a cation (+) bonded via an ionic bondwith an anion (−).

In certain embodiments, the ionic species of the HMG glucoside salt actin conjunction with other ionic tastants to modify a sensory impressionof said tastants.

In certain embodiments, the HMG glucoside compound can be combined witha salt or salt mixture. The salt or salt mixture can comprise inorganic,organic, monoatomic as well as polyatomic ions. In certain embodiments,the salts are nontoxic and edible. In certain embodiments, the salt orsalt mixtures are inorganic salts, for example, inorganic saltscomprising halogen anions or phosphate ions, alkali or earth alkalimetal salts. In certain embodiments, the salts are cationic salts suchas, but not limited to, NaCl, KCI and Na₃PO₄. In certain embodiments,the salts are anionic salts such as, but not limited to acetate salt,TFA salt, and formate salt.

3. Flavor Compositions

The flavor compositions of the present application can be used toenhance or modify the sensory experience of various edible compositionssuch as sweet goods and savory goods. The flavor compositions caninclude combinations of compounds, and can be added to ediblecompositions in various delivery system formats.

In certain embodiments, the application relates to methods formodulating the texture of an edible product comprising: a) providing atleast one comestible food product, or a precursor thereof, and b)combining the comestible food product or precursor thereof with at leasta mouth watering, lubricating, slippery and/or astringent modulatingamount of at least one flavor composition, for example, one or more HMGglucoside compound of Formula I, or a comestibly acceptable saltthereof, so as to form a modified edible food product.

In certain embodiments, the flavor compositions of the presentapplication can enhance the mouth watering, lubricating, slippery and/orastringent texture of a food product, such as, for example, an ediblecomposition including pet foods, pharmaceutical compositions and humanfoods, such as soup, a confection, and/or a snack food. In certainembodiments, the flavor compositions of the present application can beused to modify, enhance or decrease the mouth watering, lubricating,slippery and/or astringent texture of one or more of the followingsubgenuses of comestible compositions: confectioneries, bakery products,ice creams, dairy products, savory snacks, snack bars, meal replacementproducts, ready meals, soups, pastas, noodles, canned foods, frozenfoods, dried foods, chilled foods, oils and fats, baby foods, orspreads, or a mixture thereof.

In certain embodiments of the application, an edible composition can beproduced that contains a sufficient amount of at least one flavorcomposition, or its various subgenuses described herein, for example anHMG glucoside compound, for example, a compound of Formula I, to producea composition having the desired flavor, taste and/or mouthfeelcharacteristics such as “mouth watering” and/or “lubricating” and/or“slippery” and/or “astringent” characteristic.

In certain embodiments of the application, an edible composition can beproduced that contains a sufficient amount of at least one flavorcomposition, or its various subgenuses described herein, for example anHMG glucoside compound, for example a compound of Formula I, to producea composition having the desired texture characteristics such as a“mouth watering” texture.

In certain embodiments, at least a mouth watering texture modulatingamount of one or more of the flavor compositions of the presentapplication can be added to the edible food product, so that the mouthwatering texture modified edible food product has an increased ordecreased mouth watering texture as compared to the edible food productprepared without the flavor composition, as determined by human beingsor animals in general, or in the case of formulation testing, asdetermined by a taste panel of at least five human taste testers, viaprocedures known in the art.

In certain embodiments of the present application, the flavorcomposition is added to a food product in an amount effective to providea mouth watering texture.

In certain embodiments of the application, an edible composition can beproduced that contains a sufficient amount of at least one flavorcomposition, or its various subgenuses described herein, for example anHMG glucoside compound, for example a compound of Formula I, to producea composition having the desired texture characteristics such as a“lubricating” texture.

In certain embodiments, at least a lubricating texture modulating amountof one or more of the flavor compositions of the present application canbe added to the edible food product, so that the lubricating texturemodified edible food product has an increased or decreased lubricationtexture as compared to the edible food product prepared without theflavor composition, as determined by human beings or animals in general,or in the case of formulation testing, as determined by a taste panel ofat least five human taste testers, via procedures known in the art.

In certain embodiments of the present application, the flavorcomposition is added to a food product in an amount effective to providea lubricating texture.

In certain embodiments of the application, an edible composition can beproduced that contains a sufficient amount of at least one flavorcomposition, or its various subgenuses described herein, for example anHMG glucoside compound, for example a compound of Formula I, to producea composition having the desired texture characteristics such as a“slippery” texture.

In certain embodiments, at least a slippery texture modulating amount ofone or more of the flavor compositions of the present application can beadded to the edible food product, so that the slippery texture modifiededible food product has an increased or decreased slippery texture ascompared to the edible food product prepared without the flavorcomposition, as determined by human beings or animals in general, or inthe case of formulation testing, as determined by a taste panel of atleast five human taste testers, via procedures known in the art.

In certain embodiments of the present application, the flavorcomposition is added to a food product in an amount effective to providea slippery texture.

In certain embodiments of the application, an edible composition can beproduced that contains a sufficient amount of at least one flavorcomposition, or its various subgenuses described herein, for example anHMG glucoside compound, for example a compound of Formula I, to producea composition having the desired texture characteristics such as a“astringent” texture.

In certain embodiments, at least an astringent texture modulating amountof one or more of the flavor compositions of the present application canbe added to the edible food product, so that the astringent texturemodified edible food product has an increased or decreased astringenttexture as compared to the edible food product prepared without theflavor composition, as determined by human beings or animals in general,or in the case of formulation testing, as determined by a taste panel ofat least five human taste testers, via procedures known in the art.

In certain embodiments of the present application, the flavorcomposition is added to a food product in an amount effective to providea astringent texture.

In certain embodiments, the flavor composition, or any of itssubgenuses, for example, an HMG glucoside, for example, a compound ofFormula I, or a comestibly acceptable salt thereof, of the presentapplication, can be combined with an edible composition in an amounteffective to modify, enhance or otherwise alter a taste or taste profileof the edible composition. The modification can include, for example, anincrease or decrease in one or more of a sweet, sour, salty, bitter,kokumi and/or umami taste of the composition.

In certain embodiments, the flavor composition, or any of itssubgenuses, for example, an HMG glucoside, for example, a compound ofFormula I, or a comestibly acceptable salt thereof, of the presentapplication, can be combined with an edible composition in an amounteffective to modify, enhance or otherwise alter a flavor or flavorprofile of the edible composition. The modification can include, forexample, an increase or decrease in the perception of one or moresensory stimuli, such as, for example, one or more of taste (gustatory),smell (olfactory), touch (tactile) and temperature (thermal).

In certain embodiments, the flavor composition, or any of itssubgenuses, for example, an HMG glucoside, for example, a compound ofFormula I, or a comestibly acceptable salt thereof, of the presentapplication, can be combined with an edible composition in an amounteffective to modify, enhance or otherwise alter a texture profile of theedible composition.

The concentration of flavor composition admixed with an edible foodproduct to modulate or improve the flavor of the edible food product orcomposition can vary dependent on variables, such as, for example, thespecific type of edible composition, what mouth watering, lubricating,slippery and/or astringent compounds are already present in the ediblefood product and the concentrations thereof, and the enhancer effect ofthe particular flavor composition on such mouth watering, lubricating,slippery and/or astringent compounds.

In certain embodiments, admixing the flavor compositions of the presentapplication with an edible food product modulates, for example, induces,enhances or inhibits, the mouth watering, lubricating, slippery and/orastringent (or other taste or flavor properties) of other natural orsynthetic mouth watering, lubricating, slippery and/or astringentflavorants.

A broad range of concentrations of the flavor compositions can beemployed to provide such mouth watering, lubricating, slippery and/orastringent texture modification. In certain embodiments of the presentapplication, the flavor composition is admixed with a food productwherein the flavor composition is present in an amount of from about0.001 to about 500 ppb, or from about 0.005 to about 250 ppb, or fromabout 0.01 to about 200 ppb, or from about 0.05 to about 150 ppb, orfrom about 0.1 to about 100 ppb, or from about 0.5 to about 50 ppb.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product wherein the flavorcomposition is present in an amount of from between about 0.1 to about100 ppb.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product wherein the flavorcomposition is present in an amount of from about 0.01 ppm to 5000 ppm,or narrower alternative ranges from about 0.1 ppm to about 1000 ppm,from about 0.5 ppm to about 500 ppm, from about 1 ppm to about 250 ppm,from about 5 ppm to about 200 ppm, from about 10 ppm to about 150 ppm,from about 10 ppm to about 100 ppm, or from about 20 ppm to about 50ppm.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product wherein the flavorcomposition is present in an amount of from about 0.1 ppm to about 200ppm, or from about 1 ppm and about 150 ppm.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product wherein the flavorcomposition is present in an amount of 100 ppm.

In certain embodiments of the present application, the flavorcomposition is admixed with a food product wherein the flavorcomposition is present in an amount of from about 0.0000001 to about99.999% weight/weight (w/w), or from about 0.00005 to about 75% w/w, orfrom about 0.0001 to about 50% w/w, or from about 0.0005 to about 25%w/w, or from about 0.001 to about 10% w/w, or from about 0.005 to about5% w/w of the food product.

In certain embodiments, the HMG glucoside compounds of the presentapplication are blended together in various ratios or are blendedtogether with other compounds to form various flavor compositions. Incertain embodiments, the HMG glucoside compounds that are blended arecone or more compounds of Formula I. In certain embodiments, the HMGglucoside compounds and other compounds are blended together, whereineach of the HMG glucoside compounds and other compounds are present inan amount of from about 0.0000001 to about 99.999% weight/weight (w/w),or from about 0.00005 to about 75% w/w, or from about 0.0001 to about50% w/w, or from about 0.0005 to about 25% w/w, or from about 0.001 toabout 10% w/w, or from about 0.005 to about 5% w/w of the flavorcomposition.

In certain embodiments, the HMG glucoside compounds that are blendedtogether in various ratios or are blended together with other compoundsto form various flavor compositions, are, for example, compounds ofFormula I of the present application. In certain embodiments, the flavorcomposition comprises one or more HMG glucoside compound in combinationwith one or more additional compound with similar solubilities as theHMG glucoside compounds. Table 1 below provides non-limiting examples offlavor compositions comprising HMG glucosides, such as a compound ofFormula I, in combination with other additional compounds.

TABLE 1 Flavor Compositions Fl. 1 Fl. 2 Fl. 3 Fl. 4 Fl. 5 Fl. 6 Fl. 7Fl. 8 Ingredient % w/w % w/w % w/w % w/w % w/w % w/w % w/w % w/w FormulaI 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.9990-99.999 Formula II 0-99.999 0-99.999 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 Formula IIA 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 Formula II-B 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 FormulaII-C 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.9990-99.999 Formula II-D 0-99.999 0-99.999 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 Formula III 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 Formula IV 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 Formula V0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999Hydrolyzed cocoa 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 powder Hydrolyzed wheat 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 protein Hydrolyzed soy0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999protein Vanilla Extract 0-99.999 0-99.999 0-99.999 0-99.999 0-99.99910-18    0-99.999 0-99.999 Ethyl vanillin 0-99.999 0-99.999 0-99.9990-99.999 12-16    0-99.999 0-99.999 0-99.999 Ethyl maltol 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 Isoamylacetate 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 2-3   0-99.999 Ethyl acetate 0-99.999 0-99.999 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 Furaneol 0-99.999 0-99.999 0-99.999 0-99.9995-8    0-99.999 0-99.999 0-99.999 Myrcene 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 1-2    0-99.999 Linalool 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 1-3    0-99.999 0-99.999 Citral 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 Geraniol0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 1-3    0-99.999 0-99.999NaCl 99.5-99.9995   0-99.999 2.5-5     0-99.999 0-99.999 0-99.9990-99.999 0-99.999 KCl 0-99.999 99.5-99.9995   0-99.999 2.5-5    0-99.999 0-99.999 0-99.999 0-99.999 Garlic flavor 0-99.999 0-99.99914-18    0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 Onion flavor0-99.999 0-99.999 0-99.999 12-15    0-99.999 0-99.999 0-99.999 0-99.999Beef Flavor 0-99.999 0-99.999 70-80    0-99.999 0-99.999 0-99.9990-99.999 0-99.999 Chicken flavor 0-99.999 0-99.999 0-99.999 65-75   0-99.999 0-99.999 0-99.999 0-99.999 Acetic acid 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 Butyric acid0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 6-8    0-99.999 0-99.999Citric acid 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.99995-98    42-48    Lactic acid 0-99.999 0-99.999 0-99.999 0-99.99950-65    70-80    0-99.999 0-99.999 Malic acid 0-99.999 0-99.9990-99.999 0-99.999 0-99.999 0-99.999 0-99.999 28-32    Tartaric acid0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 20-25   Other base flavor 0-99.999 0-99.999 0-99.999 0-99.999 0-99.999 0-99.9990-99.999 0-99.999 compounds

4. Delivery Systems

In certain embodiments, the flavor compositions of the presentapplication can be incorporated into a delivery system for use in ediblecompositions. In certain embodiments, the composition will compriseanother flavor, taste or texture modifier such as a mouth watering,lubricating, slippery and/or astringent flavorant. Delivery systems canbe liquid or solid, aqueous or non-aqueous. Delivery systems aregenerally adapted to suit the needs of the flavor composition and/or theedible composition into which the flavor composition will beincorporated.

The flavoring compositions can be employed in liquid form, dried form,and/or solid form. When used in dried form, suitable drying means suchas spray drying can be used. Alternatively, a flavoring composition canbe encapsulated or absorbed onto water soluble materials, including butnot limited to materials such as cellulose, starch, sugar, maltodextrin,gum arabic and so forth. The actual techniques for preparing such driedforms are well-known in the art, and can be applied to the presentlydisclosed subject matter.

The flavoring compositions of the presently disclosed subject matter canbe used in many distinct physical forms well known in the art to providean initial burst of taste, flavor and/or texture; and/or a prolongedsensation of taste, flavor and/or texture. Without being limitedthereto, such physical forms include free forms, such as spray dried,powdered, and beaded forms, and encapsulated forms, and mixturesthereof.

In specific embodiments, as noted above, encapsulation techniques can beused to modify the flavor systems. In certain embodiments, flavorcompounds, flavor components, or the entire flavor system can be fullyor partially encapsulated. Encapsulating materials and/or techniques canbe selected to determine the type of modification of the flavor system.

In specific embodiments, the encapsulating materials and/or techniquesare selected to improve the stability of the flavor compounds, flavorcomponents, or flavor systems; while in other embodiments theencapsulating materials and/or techniques are selected to modify therelease profile of the flavor compounds, flavor components, or flavorsystems.

Suitable encapsulating materials can include, but are not limited to,hydrocolloids such as alginates, pectins, agars, guar gums, celluloses,and the like, proteins, polyvinyl acetate, polyethylene, crosslinkedpolyvinyl pyrrolidone, polymethylmethacrylate, polylactidacid,polyhydroxyalkanoates, ethylcellulose, polyvinyl acetatephthalate,polyethylene glycol esters, methacrylicacid-co-methylmethacrylate,ethylene-vinylacetate (EVA) copolymer, and the like, and combinationsthereof. Suitable encapsulating techniques can include, but are notlimited to, spray coating, spray drying, spray chilling, absorption,adsorption, inclusion complexing (e.g., creating a flavor/cyclodextrincomplex), coacervation, fluidized bed coating, or other process can beused to encapsulate an ingredient with an encapsulating material.

Encapsulated delivery systems for flavoring agents or sweetening agentscontain a hydrophobic matrix of fat or wax surrounding a sweeteningagent or flavoring agent core. The fats can be selected from any numberof conventional materials such as fatty acids, glycerides or polyglycerol esters, sorbitol esters, and mixtures thereof. Examples offatty acids include but are not limited to hydrogenated and partiallyhydrogenated vegetable oils such as palm oil, palm kernel oil, peanutoil, rapeseed oil, rice bran oil, soybean oil, cottonseed oil, sunfloweroil, safflower oil, and mixtures thereof. Examples of glycerides includebut are not limited to monoglycerides, diglycerides, and triglycerides.

Waxes useful can be chosen from the group consisting of natural andsynthetic waxes, and mixtures thereof. Non-limiting examples includeparaffin wax, petrolatum, carbowax, microcrystalline wax, beeswax,carnauba wax, candelilla wax, lanolin, bayberry wax, sugarcane wax,spermaceti wax, rice bran wax, and mixtures thereof.

The fats and waxes can be use individually or in combination in amountsvarying from about 10 to about 70%, and alternatively in amounts fromabout 30 to about 60%, by weight of the encapsulated system. When usedin combination, the fat and wax are preferably present in a ratio fromabout 70:10 to 85:15, respectively.

Typical encapsulated flavor compositions, flavoring agent or sweeteningagent delivery systems are disclosed in U.S. Pat. Nos. 4,597,970 and4,722,845, the disclosures of which are incorporated herein by referencein their entireties.

Liquid delivery systems can include, but are not limited to, systemswith a dispersion of HMG glucoside compound(s) or the flavorcompositions of the present application, such as in carbohydrate syrupsand/or emulsions. Liquid delivery systems can also include extractswhere the HMG glucoside compound(s) and/or the flavor compositions aresolubilized in a solvent. Solid delivery systems can be created by spraydrying, spray coating, spray chilling, fluidized bed drying, absorption,adsorption, coacervation, complexation, or any other standard technique.In some embodiments, the delivery system can be selected to becompatible with or to function in the edible composition. In someembodiments, the delivery system will include an oleaginous materialsuch as a fat or oil. In some embodiments, the delivery system willinclude a confectionery fat such as cocoa butter, a cocoa butterreplacer, a cocoa butter substitute, or a cocoa butter equivalent.

When used in dried form, suitable drying means such as spray drying maybe used. Alternatively, a flavoring composition may be adsorbed orabsorbed onto substrates such as water soluble materials, such ascellulose, starch, sugar, maltodextrin, gum arabic and so forth or maybe encapsulated. The actual techniques for preparing such dried formsare well known in the art.

5. End Product Systems

The flavoring compositions of the present disclosed subject matter canbe used in a wide variety of ingestible vehicles. Non-limiting examplesof suitable ingestible vehicles include chewing gum compositions, hardand soft confections, dairy products, beverage products including juiceproducts and soft drinks, pharmaceuticals, bakery goods, frozen foods,food products and food categories described herein. The combination ofthe flavoring composition of the presently disclosed subject mattertogether with an ingestible vehicle and optional ingredients, whendesired, provides a flavoring agent that possesses unexpected taste,flavor and/or texture value and imparts, for example, a mouth watering,lubricating, slippery and/or astringent sensory experience.

In the method for flavoring an ingestible composition of the presentlydisclosed subject matter, the ingestible composition is prepared byadmixing the flavoring agent in an ingestible vehicle, together with anyoptional ingredients, to form a uniform mixture. The final compositionsare readily prepared using standard methods and apparatus generallyknown by those skilled in the corresponding arts, such as confectionaryarts. The apparatus useful in accordance with the presently disclosedsubject matter comprises mixing apparatus well known in the art, andtherefore the selection of the specific apparatus will be apparent tothe artisan.

In certain embodiments, the present application relates to the modifiededible food products produced by the methods disclosed herein. Incertain embodiments, the food products can be produced by processes forproducing comestible products well known to those of ordinary skill inthe art, wherein the flavor composition of the present application isemployed as a mouth watering, lubricating, slippery and/or astringenttexture enhancer for the food product.

The flavor composition and its various subgenuses can be combined withor applied to a comestible or medicinal products or precursor thereof inany of innumerable ways known to cooks the world over, or producers ofcomestible or medicinal products. For example, the flavor compositionscan be dissolved in or dispersed in one of many known comestiblyacceptable liquids, solids, or other carriers, such as water at neutral,acidic, or basic pH, fruit or vegetable juices, vinegar, marinades,beer, wine, natural water/fat emulsions such as milk or condensed milk,whey or whey products, edible oils and shortenings, fatty acids, certainlow molecular weight oligomers of propylene glycol, glyceryl esters offatty acids, and dispersions or emulsions of such hydrophobic substancesin aqueous media, salts such as sodium chloride, vegetable flours,solvents such as ethanol, solid edible diluents such as vegetablepowders or flours, and the like, and then combined with precursors ofthe comestible or medicinal products, or applied directly to thecomestible or medicinal products.

In certain embodiments, the flavor compositions of the presentapplication can be admixed with foods, beverages and other comestiblecompositions wherein savory compounds, especially NaCl, MSG, inosinemonophosphate (IMP), or guanosine monophosphate (GMP) are conventionallyutilized. These compositions include compositions for human and animalconsumption, for example, food or drinks (liquids) for consumption byagricultural animals, pets and zoo animals. Those of ordinary skill inthe art of preparing and selling comestible compositions (i.e., ediblefoods or beverages, or precursors or flavor modifiers thereof) are wellaware of a large variety of classes, subclasses and species of thecomestible compositions, and utilize well-known and recognized terms ofart to refer to those comestible compositions while endeavoring toprepare and sell various of those comestible compositions. Such a listof terms of art is enumerated below, and it is specifically contemplatedhereby that the flavor compositions of the present application can beused to modify or enhance the mouth watering, lubricating, slipperyand/or astringent mouthfeel of the following list edible compositions,either singly or in all reasonable combinations or mixtures thereof.

In certain embodiments, the food products to which the flavorcompositions of the present application are admixed with comprise, byway of example, the wet soup category, the dehydrated and culinary foodcategory, the beverage category, the frozen food category, the snackfood category, and seasonings or seasoning blends, described herein.

In other embodiments, the flavor compositions of the present applicationare admixed with one or more confectioneries, chocolate confectionery,tablets, countlines, bagged selfmies/softlines, boxed assortments,standard boxed assortments, twist wrapped miniatures, seasonalchocolate, chocolate with toys, allsorts, other chocolate confectionery,mints, standard mints, power mints, boiled sweets, pastilles, gums,jellies and chews, toffees, caramels and nougat, medicatedconfectionery, lollipops, liquorice, other sugar confectionery, gum,chewing gum, sugarised gum, sugar-free gum, functional gum, bubble gum,bread, packaged/industrial bread, unpackaged/artisanal bread, pastries,cakes, packaged/industrial cakes, unpackaged/artisanal cakes, cookies,chocolate coated biscuits, sandwich biscuits, filled biscuits, savorybiscuits and crackers, bread substitutes, breakfast cereals, rtecereals, family breakfast cereals, flakes, muesli, other rte cereals,children's breakfast cereals, hot cereals, ice cream, impulse ice cream,single portion dairy ice cream, single portion water ice cream,multi-pack dairy ice cream, multi-pack water ice cream, take-home icecream, take-home dairy ice cream, ice cream desserts, bulk ice cream,take-home water ice cream, frozen yoghurt, artisanal ice cream, dairyproducts, milk, fresh/pasteurized milk, full fat fresh/pasteurized milk,semi skimmed fresh/pasteurized milk, long-life/uht milk, full fat longlife/uht milk, semi skimmed long life/uht milk, fat-free long life/uhtmilk, goat milk, condensed/evaporated milk, plain condensed/evaporatedmilk, flavored, functional and other condensed milk, flavored milkdrinks, dairy only flavored milk drinks, flavored milk drinks with fruitjuice, soy milk, sour milk drinks, fermented dairy drinks, coffeewhiteners, powder milk, flavored powder milk drinks, cream, cheese,processed cheese, spreadable processed cheese, unspreadable processedcheese, unprocessed cheese, spreadable unprocessed cheese, hard cheese,packaged hard cheese, unpackaged hard cheese, yoghurt, plain/naturalyoghurt, flavored yoghurt, fruited yoghurt, probiotic yoghurt, drinkingyoghurt, regular drinking yoghurt, probiotic drinking yoghurt, chilledand shelf-stable desserts, dairy-based desserts, soy-based desserts,chilled snacks, fromage frais and quark, plain fromage frais and quark,flavored fromage frais and quark, savory fromage frais and quark, sweetand savory snacks, fruit snacks, chips/crisps, extruded snacks,tortilla/corn chips, popcorn, pretzels, nuts, other sweet and savorysnacks, snack bars, granola bars, breakfast bars, energy bars, fruitbars, other snack bars, meal replacement products, slimming products,convalescence drinks, ready meals, canned ready meals, frozen readymeals, dried ready meals, chilled ready meals, dinner mixes, frozenpizza, chilled pizza, soup, canned soup, dehydrated soup, instant soup,chilled soup, uht soup, frozen soup, pasta, canned pasta, dried pasta,chilled/fresh pasta, noodles, plain noodles, instant noodles, cups/bowlinstant noodles, pouch instant noodles, chilled noodles, snack noodles,canned food, canned meat and meat products, canned fish/seafood, cannedvegetables, canned tomatoes, canned beans, canned fruit, canned readymeals, canned soup, canned pasta, other canned foods, frozen food,frozen processed red meat, frozen processed poultry, frozen processedfish/seafood, frozen processed vegetables, frozen meat substitutes,frozen potatoes, oven baked potato chips, other oven baked potatoproducts, non-oven frozen potatoes, frozen bakery products, frozendesserts, frozen ready meals, frozen pizza, frozen soup, frozen noodles,other frozen food, dried food, dessert mixes, dried ready meals,dehydrated soup, instant soup, dried pasta, plain noodles, instantnoodles, cups/bowl instant noodles, pouch instant noodles, chilled food,chilled processed meats, chilled fish/seafood products, chilledprocessed fish, chilled coated fish, chilled smoked fish, chilled lunchkit, chilled ready meals, chilled pizza, chilled soup, chilled/freshpasta, chilled noodles, oils and fats, olive oil, vegetable and Seedoil, cooking fats, butter, margarine, spreadable oils and fats,functional spreadable oils and fats, sauces, dressings and condiments,tomato pastes and purees, bouillon/stock cubes, stock cubes, gravygranules, liquid stocks and fonds, herbs and spices, fermented sauces,soy based sauces, pasta sauces, wet sauces, dry sauces/powder mixes,ketchup, mayonnaise, regular mayonnaise, mustard, salad dressings,regular salad dressings, low fat salad dressings, vinaigrettes, dips,pickled products, other sauces, dressings and condiments, baby food,milk formula, standard milk formula, follow-on milk formula, toddlermilk formula, hypoallergenic milk formula, prepared baby food, driedbaby food, other baby food, spreads, jams and preserves, honey,chocolate spreads, nut-based spreads, and yeast-based spreads.

5.1 Sweet Goods

5.1.1 Chewing Gum

The flavor systems can be used in sugarless gum formulations and canalso be used in a sugar chewing gum. The flavor systems can be used ineither regular chewing gum or bubble gum. Various specifics of chewinggum compositions are disclosed in U.S. Pat. No. 6,899,911, thedisclosure of which is incorporated herein by reference in its entirety.

The chewing gum composition of the presently disclosed subject matterfollows the general pattern outlined below. In general, a chewing gumcomposition typically contain a chewable gum base portion which isessentially free of water and is water-insoluble, a water-soluble bulkportion and flavors which are typically water insoluble. Thewater-soluble portion dissipates with a portion of the flavor over aperiod of time during chewing. The gum base portion is retained in themouth throughout the chew.

The insoluble gum base generally comprises elastomers, elastomersolvents, plasticizers, waxes, emulsifiers and inorganic fillers.Plastic polymers, such as polyvinyl acetate, which behave somewhat asplasticizers, are also often included. Other plastic polymers that canbe used include polyvinyl laureate, polyvinyl alcohol and polyvinylpyrrolidone.

Elastomers can include polyisobutylene, butyl rubber,(isobutylene-isoprene copolymer) and styrene butadiene rubber, as wellas natural latexes such as chicle. Elastomer solvents are often resinssuch as terpene resins. Plasticizers, sometimes called softeners, aretypically fats and oils, including tallow, hydrogenated and partiallyhydrogenated vegetable oils, and cocoa butter. Commonly employed waxesinclude paraffin, microcrystalline and natural waxes such as beeswax andcarnauba. Microcrystalline waxes, especially those with a high degree ofcrystallinity, can be considered bodying agents or textural modifiers.

According to the preferred embodiment of the presently disclosed subjectmatter, the insoluble gum base constitutes between about 5% to about 95%by weight of the gum. More preferably the insoluble gum base comprisesbetween 10% and 50% by weight of the gum and most preferably about 20%to 35% by weight of the gum.

The gum base typically also includes a filler component. The fillercomponent can be calcium carbonate, magnesium carbonate, talc, dicalciumphosphate or the like. The filler can constitute between about 5% andabout 60% by weight of the gum base. Preferably the filler comprisesabout 5% to 50% by weight of the gum base.

Gum bases typically also contain softeners including glycerolmonostearate and glycerol triacetate. Gum bases can also containoptional ingredients such as antioxidants, colors, and emulsifiers. Thepresently disclosed subject matter contemplates employing anycommercially acceptable gum base.

The water-soluble portion of the chewing gum can further comprisesofteners, sweeteners, flavors, physiological cooling agents andcombinations thereof. The sweeteners often fulfill the role of bulkingagents in the gum. The bulking agents typically comprise about 5% toabout 95% of the gum composition.

Softeners are added to the chewing gum in order to optimize thechewability and mouth feel of the gum. Softeners, also known in the artas plasticizers or plasticizing agents, generally constitute betweenabout 0.5% to about 15% of the chewing gum. Softeners contemplated bythe presently disclosed subject matter include glycerin, lecithin andcombinations thereof. Further, aqueous sweetener solutions such as thosecontaining sorbitol, hydrogenated starch hydrolysate, corn syrup andcombinations thereof can be used as softeners and binding agents in gum.

As mentioned above, the flavor systems of the presently disclosedsubject matter can be used in sugarless gum formulations. However,formulations containing sugar are also within the scope of theinvention. Sugar sweeteners generally include saccharide-containingcomponents commonly known in the chewing gum art which comprise, but arenot limited to, sucrose, dextrose, maltose, dextrin, dried invert sugar,fructose, galactose, corn syrup solids and the like, alone or in anycombination.

The flavor systems of the presently disclosed subject matter can also beused in combination with sugarless sweeteners. Generally sugarlesssweeteners include components with sweetening characteristics but whichare devoid of the commonly known sugars and comprise, but are notlimited to, sugar alcohols such as sorbitol, hydrogenated isomaltulose,mannitol, xylitol, lactitol, erythritol, hydrogenated starchhydrolysate, maltitol and the like alone or in any combination

Depending on the particular sweetness release profile andshelf-stability needed, coated or uncoated high-intensity sweeteners canbe used in the chewing gum composition, or can be used in a coatingapplied to centers made from those gum compositions. High-intensitysweeteners, preferably aspartame, can be used at levels from about 0.01%to about 3.0%. Encapsulated aspartame is a high intensity sweetener withimproved stability and release characteristics, as compared to freeaspartame. Free aspartame can also be added, and a combination of somefree and encapsulated aspartame is preferred when aspartame is used.Other high intensity sweeteners that can be used in the gum center are:saccharin, Thaumatin, alitame, saccharin salts, sucralose, Stevia, andacesulfame K. Overall, the chewing gum composition will preferablecomprise about 0.5% to about 90% sweetening agents. Most typically thesweetening agents will comprises at least one bulk sweetener and atleast one high-intensity sweetener.

Optional ingredients such as colors, emulsifiers and pharmaceuticalagents can also be added as separate components of the chewing gumcomposition, or added as part of the gum base.

Aqueous syrups, such as corn syrup and hydrogenated corn syrup can beused, particularly if their moisture content is reduced. This canpreferably be done by coevaporating the aqueous syrup with aplasticizer, such as glycerin or propylene glycol, to a moisture contentof less than 10%. Preferred compositions include hydrogenated starchhydrolysate solids and glycerin. Such syrups and their methods ofpreparation are discussed in detail in U.S. Pat. No. 4,671,967.

A preferred method of manufacturing chewing gum according to thepresently disclosed subject matter is by sequentially adding the variouschewing gum ingredients to any commercially available mixer known in theart. After the ingredients have been thoroughly mixed, the gum isdischarged from the mixer and shaped into the desired form such as byrolling into sheets and cutting into sticks, extruding into chunks, orcasting into pellets.

Generally, the ingredients are mixed by first melting the gum base andadding it to the running mixer. The base can also be melted in the mixeritself. Color or emulsifiers can also be added at this time, along withsyrup and a portion of the bulking agent. Further portions of thebulking agent can then be added to the mixer. Flavor systems aretypically added with the final portion of the bulking agent. If theflavor system is coated or otherwise modified as when incorporated intoa delivery system to modify its release rate, it will preferably beadded after the final portion of bulking agent has been added. Theentire mixing procedure typically takes from five to twenty minutes, butlonger mixing times can sometime be required. Those skilled in the artwill recognize that many variations of the above described procedurescan be followed.

If formed into pellets or balls, the chewing gum composition can becoated. The coating is initially present as a liquid syrup whichcontains from about 30% to about 80% or 85% sugars or sugar alcohols,and from about 15% or 20% to about 70% of a solvent such as water. Ingeneral, the coating process is carried out in conventional panningequipment. Gum center tablets to be coated are placed into the panningequipment to form a moving mass.

The material or syrup which will eventually form the coating is appliedor distributed over the gum center tablets. The flavor systems of thepresently disclosed subject matter can be added before, during and afterapplying the syrup to the gum centers. Once the coating has dried toform a hard surface, additional syrup additions can be made to produce aplurality of coatings or multiple layers of coating. The flavor systemscan be added to any or none of the coatings and/or layers.

In the panning procedure, syrup is added to the gum center tablets at atemperature range of from about 100° F. to about 240° F. Preferably, thesyrup temperature is from about 140° F. to about 200° F. Mostpreferably, the syrup temperature should be kept constant throughout theprocess in order to prevent the polyol in the syrup from crystallizing.The syrup can be mixed with, sprayed upon, poured over, or added to thegum center tablets in any way known to those skilled in the art.

In another embodiment, a soft coating is formed by adding a powdercoating after a liquid coating. The powder coating can include naturalcarbohydrate gum hydrolysates, maltodextrin, gelatin, cellulosederivatives, starches, modified starches, sugars, sugar alcohols,natural carbohydrate gums and fillers like talc and calcium carbonate.

Each component of the coating on the gum center can be applied in asingle layer or in a plurality of layers. In general, a plurality oflayers is obtained by applying single coats, allowing the layers to dry,and then repeating the process. The amount of solids added by eachcoating step depends chiefly on the concentration of the coating syrup.Any number of coats can be applied to the gum center tablet. Preferably,no more than about 75 coats are applied to the gum center. Morepreferably, less than about 60 coats are applied and most preferably,about 30 to about 60 coats are applied. In any event, the presentlydisclosed subject matter contemplates applying an amount of syrupsufficient to yield a coated chewing gum product containing about 10% toabout 65% coating. Preferably, the final product will contain from about20% to about 50% coating.

Those skilled in the art will recognize that in order to obtain aplurality of coated layers, a plurality of premeasured aliquots ofcoating syrup can be applied to the gum center. It is contemplated,however, that the volume of aliquots of syrup applied to the gum centercan vary throughout the coating procedure.

Once a coating of syrup is applied to the gum center, the syrup is driedin an inert medium. A preferred drying medium comprises air. Preferably,forced drying air contacts the wet syrup coating in a temperature rangeof from about 70° F. to about 110° F. More preferably, the drying air isin the temperature range of from about 80° F. to about 100° F. Theinvention also contemplates that the drying air possesses a relativehumidity of less than about 15 percent. Preferably, the relativehumidity of the drying air is less than about 8%.

The drying air can be passed over and admixed with the syrup coated gumcenters in any way commonly known in the art. Preferably, the drying airis blown over and around the syrup coated gum center at a flow rate, forlarge scale operations, of about 2800 cubic feet per minute. If lowerquantities of material are being processed, or if smaller equipment isused, lower flow rates would be used. If a flavor is applied after asyrup coating has been dried, the presently disclosed subject mattercontemplates drying the flavor with or without the use of a dryingmedium.

The amount of flavoring agent employed herein is normally a matter ofpreference subject to such factors as the type of final chewing gumcomposition, the individual flavor, the gum base employed, and thestrength of flavor desired. Thus, the amount of flavoring can be variedin order to obtain the result desired in the final product and suchvariations are within the capabilities of those skilled in the artwithout the need for undue experimentation. In gum compositions, theflavoring agent is generally present in amounts from about 0.02% toabout 5%, and preferably from about 0.1% to about 2%, and morepreferably, from about 0.8% to about 1.8%, by weight of the chewing gumcomposition.

5.1.2 Sugar Confectionary

Another important aspect of the presently disclosed subject matterincludes a confectionery composition incorporating the inventiveflavoring agent and a method for preparing the confectionerycompositions. The preparation of confectionery formulations iswell-known in the art. Confectionery items have been classified aseither “hard” confectionery or “soft” confectionery. The flavoringagents of the presently disclosed subject matter can be incorporatedinto the confections by admixing the compositions of the presentlydisclosed subject matter into the conventional hard and softconfections.

Hard confectionery can be processed and formulated by conventionalmeans. In general, a hard confectionery has a base composed of a mixtureof sugar and other carbohydrate bulking agents kept in an amorphous orglassy condition. The hard confectionery can also be sugarless. Thisform is considered a solid syrup of sugars generally having from about0.5% to about 1.5% moisture. Such materials normally contain up to about92% sugar, up to about 55% corn syrup and from about 0.1% to about 5%water, by weight of the final composition. The syrup component isgenerally prepared from sucrose and corn syrups, but can include othermaterials. Further ingredients such as flavorings, sweetening agents,acidulants, colorants and so forth can also be added.

Such confectionery can be routinely prepared by conventional methods,including but not limited to methods involving fire cookers, vacuumcookers, and scraped-surface cookers also referred to as high speedatmospheric cookers. The apparatus useful in accordance with thepresently disclosed subject matter comprises cooking and mixingapparatus well known in the confectionery manufacturing arts, andtherefore the selection of the specific apparatus will be apparent tothe artisan.

Fire cookers involve the traditional method of making a candy base. Inthis method, the desired quantity of carbohydrate bulking agent isdissolved in water by heating the agent in a kettle until the bulkingagent dissolves. Additional bulking agent can then be added and cookeduntil a final temperature of 145° C. to 156° C. is achieved. The batchis then cooled and worked as a plastic-like mass to incorporateadditives such as flavoring agent, colorants and the like.

A high-speed atmospheric cooker uses a heat-exchanger surface, whichinvolves spreading a film of candy on a heat exchange surface, the candyis heated to 165° C. to 170° C. within a few seconds. The candy is thenrapidly cooled to 100° C. to 120° C. and worked as a plastic-like massenabling incorporation of the additives, such as flavoring agent,colorants and the like. In vacuum cookers, the carbohydrate bulkingagent is boiled to 125° C. to 132° C., vacuum is applied and additionalwater is boiled off without extra heating. When cooking is complete, themass is a semi-solid and has a plastic-like consistency. At this point,flavoring agent, colorants, and other additives are admixed in the massby routine mechanical mixing operations.

The optimum mixing required to uniformly mix the flavoring agent,colorants and other additives during conventional manufacturing of hardconfectionery is determined by the time needed to obtain a uniformdistribution of the materials. Generally, mixing times of from 2 to 10minutes have been found to be acceptable.

Once the candy mass has been properly tempered, it can be cut intoworkable portions or formed into desired shapes. A variety of formingtechniques can be utilized depending upon the shape and size of thefinal product desired. A general discussion of the composition andpreparation of hard confections can be found in H. A. Lieberman,Pharmaceutical Dosage Forms: Tablets, Volume 1 (1989), Marcel Dekker,Inc., New York, N.Y. at pages 419 to 582, which disclosure isincorporated herein by reference.

Compressed tablet confections contain particular materials and areformed into structures under pressure. These confections generallycontain sugars in amounts up to about 95%, by weight of the composition,and typical tablet excipients such as binders and lubricants as well asflavoring agent, colorants and so forth. These confections can also besugarless.

Similar to hard confectionery, soft confectionery can be utilized in theembodiments of the disclosed subject matter. The preparation of softconfections, such as nougat, involves conventional methods, such as thecombination of two primary components, namely (1) a high boiling syrupsuch as a corn syrup, or the like, and (2) a relatively light texturedfrappe, generally prepared from egg albumin, gum arabic, gelatin,vegetable proteins, such as soy derived compounds, sugarless milkderived compounds such as milk proteins, and mixtures thereof. Thefrappe is generally relatively light, and can, for example, range indensity from about 0.5 to about 0.7 grams/cc.

The high boiling syrup, or “bob syrup” of the soft confectionery isrelatively viscous and has a higher density than the frappe component,and frequently contains a substantial amount of carbohydrate bulkingagent. Conventionally, the final nougat composition is prepared by theaddition of the “bob syrup” to the frappe under agitation, to form thebasic nougat mixture. Further ingredients such as flavoring, additionalcarbohydrate bulking agent, colorants, preservatives, medicaments,mixtures thereof and the like can be added thereafter also underagitation. Soft confectioneries can also be prepared sugarless. Ageneral discussion of the composition and preparation of nougatconfections can be found in B. W. Minifie, Chocolate, Cocoa andConfectionery: Science and Technology, 2nd edition, AVI Publishing Co.,Inc., Westport, Conn. (1983), at pages 576-580, which disclosure isincorporated herein by reference.

In general, the frappe component is prepared first and thereafter thesyrup component is slowly added under agitation at a temperature of atleast about 65° C., and preferably at least about 100° C. The mixture ofcomponents is continued to be mixed to form a uniform mixture, afterwhich the mixture is cooled to a temperature below 80° C., at whichpoint, the flavor can be added. The mixture is further mixed for anadditional period until it is ready to be removed and formed intosuitable confectionery shapes.

In accordance with this invention, effective amounts of the flavoringagents of the presently disclosed subject matter can be admixed into thehard and soft confections. The exact amount of flavoring agent employedis normally a matter of preference subject to such factors as theparticular type of confection being prepared, the type of bulking agentor carrier employed, the type of flavor employed and the intensity ofbreath freshening perception desired. Thus, the amount of flavoringagent can be varied in order to obtain the result desired in the finalproduct and such variations are within the capabilities of those skilledin the art without the need for undue experimentation. In general, theamount of flavoring agent normally present in a hard or soft confectionwill be from about 0.001% to about 20%, preferably from about 0.01% toabout 15%, more preferably from about 0.01% to about 10%, and morepreferably from about 0.01% to about 5%, and more preferably 0.01% toabout 0.5% by weight of the confection.

The presently disclosed subject matter extends to methods for making theimproved confections. The flavoring agents can be incorporated into anotherwise conventional hard or soft confection composition usingstandard techniques and equipment known to those skilled in the art. Theapparatus useful in accordance with the presently disclosed subjectmatter comprises mixing and heating apparatus well known in theconfectionery manufacturing arts, and therefore the selection of thespecific apparatus will be apparent to the artisan.

In such a method, a composition is made by admixing the inventiveflavoring agent into the confectionery composition along with the otheringredients of the final desired composition. Other ingredients willusually be incorporated into the composition as dictated by the natureof the desired composition as well known by those having ordinary skillin the art. The ultimate confectionery compositions are readily preparedusing methods generally known in the food technology and pharmaceuticalarts. Thereafter the confectionery mixture can be formed into desirableconfectionery shapes.

The flavoring agents can be formulated with conventional ingredientswhich offer a variety of textures to suit particular applications. Suchingredients can be in the form of hard and soft confections, tablets,toffee, nougat, chewy candy, chewing gum and so forth, center filledcandies, both sugar and sugarless. The acceptable ingredients can beselected from a wide range of materials. Without being limited thereto,such materials include diluents, binders and adhesives, lubricants,disintegrants, bulking agents, humectants and buffers and adsorbents.The preparation of such confections and chewing gum products is wellknown.

5.1.3. Chocolates and Fillings

The presently disclosed subject matter is also used with and/or inchocolate products, chocolate-flavored confections, and chocolateflavored compositions. Chocolates also include those containing crumbsolids or solids fully or partially made by a crumb process. Variouschocolates are disclosed, for example, in U.S. Pat. Nos. 7,968,140 and8,263,168, the disclosures of which are incorporated herein by referencein their entireties. A general discussion of the composition andpreparation of chocolate confections can be found in B. W. Minifie,Chocolate, Cocoa and Confectionery: Science and Technology, 2nd edition,AVI Publishing Co., Inc., Westport, Conn. (1982), which disclosure isincorporated herein by reference.

The term “chocolate” as used herein refers to a solid or semi-plasticfood and is intended to refer to all chocolate or chocolate-likecompositions containing a fat-based component phase or fat-likecomposition. The term is intended to include standardized ornonstandardized compositions conforming to the U.S.

Standards Of Identity (SOI), CODEX Alimentarius and/or otherinternational standards and compositions not conforming to the U.S.Standards Of Identity or other international standards. The termincludes dark chocolate, baking chocolate, sweet chocolate, bittersweetor semisweet chocolate, milk chocolate, buttermilk chocolate, skim milkchocolate, mixed dairy product chocolate, white chocolate, sweet cocoaand vegetable fat coating, sweet chocolate and vegetable fat coating,milk chocolate and vegetable fat coating, vegetable fat based coating,pastels including white chocolate or coating made with cocoa butter orvegetable fat or a combination of these, nutritionally modifiedchocolate-like compositions (chocolates or coatings made with reducedcalorie ingredients) and low fat chocolates, aerated chocolates,compound coatings, non-standardized chocolates and chocolate-likecompositions, unless specifically identified otherwise.

Nonstandardized chocolates result when, for example, the nutritivecarbohydrate sweetener is replaced partially or completely; or when thecocoa butter, cocoa butter alternative, cocoa butter equivalent, cocoabutter extender, cocoa butter replacer, cocoa butter substitute ormilkfat are replaced partially or completely; or when components thathave flavors that imitate milk, butter or chocolate are added or otheradditions or deletions in formula are made outside the FDA standards ofidentify of chocolate or combinations thereof. Chocolate-likecompositions are those fat-based compositions that can be used assubstitutes for chocolate in applications such as panning, molding, orenrobing; for example, carob.

In the United States, chocolate is subject to a standard of identityestablished by the U.S. Food and Drug Administration (FDA) under theFederal Food, Drug and Cosmetic Act. Definitions and standards for thevarious types of chocolate are well established in the U.S.Nonstandardized chocolates are those chocolates which have compositionsthat fall outside the specified ranges of the standardized chocolates.

The chocolate can contain a sugar syrup/solids, invert sugar, hydrolyzedlactose, maple sugar, brown sugar, molasses, honey, sugar substitute andthe like. The term “sugar substitute” includes bulking agents, sugaralcohols (polyols such as glycerol), or high potency sweeteners orcombinations thereof. Nutritive carbohydrate sweeteners with varyingdegrees of sweetness intensity can be any of those typically used in theart and include, but are not limited to, sucrose, e.g. from cane orbeet, dextrose, fructose, lactose, maltose, glucose syrup solids, cornsyrup solids, invert sugar, hydrolyzed lactose, honey, maple sugar,brown sugar, molasses and the like. Sugar substitutes can partiallyreplace the nutritive carbohydrate sweetener. High potency sweetenersinclude aspartame, cyclamates, saccharin, acesulfame-K, neohesperidindihydrochalcone, sucralose, alitame, stevia sweeteners, glycyrrhizin,thaumatin and the like and mixtures thereof. The preferred high potencysweeteners are aspartame, cyclamates, saccharin, and acesulfame-K.Examples of sugar alcohols can be any of those typically used in the artand include sorbitol, mannitol, xylitol, maltitol, isomalt, lactitol andthe like.

The chocolates can also contain bulking agents. The term “bulkingagents” as defined herein can be any of those typically used in the artand include polydextrose, cellulose and its derivatives, maltodextrin,gum arabic, and the like.

The chocolate products can contain emulsifiers. Examples of safe andsuitable emulsifiers can be any of those typically used in the art andinclude lecithin derived from vegetable sources such as soybean,safflower, corn, etc., fractionated lecithins enriched in eitherphosphatidyl choline or phosphatidyl ethanolamine, or both, mono- anddigylcerides, diacetyl tartaric acid esters of mono- and diglycerides(also referred to as DATEM), monosodium phosphate derivatives of mono-and diglycerides of edible fats or oils, sorbitan monostearate,hydroxylated lecithin, lactylated fatty acid esters of glycerol andpropylene glycol, polyglycerol esters of fatty acids, propylene glycolmono- and di-esters of fats and fatty acids, or emulsifiers that canbecome approved for the US FDA-defined soft candy category. In addition,other emulsifiers that can be used include polyglycerol polyricinoleate(PGPR), ammonium salts of phosphatidic acid, (e.g. YN) sucrose esters,oat extract, etc., any emulsifier found to be suitable in chocolate orsimilar fat/solid system or any blend.

The term “chocolate-flavored confection” refers to food products,excluding “chocolate”, having a chocolate flavor/aroma and comprising acocoa fraction. These products are stable at ambient temperatures forextended periods of time (e.g., greater than 1 week) and arecharacterized as microbiologically shelf-stable at 18-30° C. undernormal atmospheric conditions. Examples include chocolate-flavored hardcandies, chewables, chewing gums, etc.

The term “chocolate-flavored compositions” refers to chocolate-flavoredcompositions, excluding “chocolate”, containing a cocoa fraction andhaving a chocolate flavor/aroma. Examples include chocolate-flavoredcake mixes, ice creams, syrups, baking goods, etc. The term includeschocolate-flavored compositions (e.g., cakes, nougats, puddings, etc.),as well as compositions not having a chocolate-flavor (e.g., caramels,etc.).

5.2 Savory Goods and Other Food Products

In certain embodiments, the flavor compositions of the presentapplication are incorporated into savory goods to impart, enhance, ormodify a mouth watering, lubricating, slippery and/or astringentmouthfeel. In certain embodiments, a savory good is a food product thathas savory flavors including, for example, but not limited to, spicyflavor, pepper flavor, dairy flavor, vegetable flavor, tomato flavor,dill flavor, meat flavor, poultry flavor, chicken flavor and reactionflavors that are added or generated during heating of a food product.

In certain embodiments, the flavor compositions are incorporated into awet soup category food product, which comprises wet/liquid soupsregardless of concentration or container, including frozen soups. Incertain embodiments, the a soup food product means a food prepared frommeat, poultry, fish, vegetables, grains, fruit and/or other ingredients,cooked in a liquid which may include visible pieces of some or all ofthese ingredients. It may be clear (as a broth) or thick (as a chowder),smooth, pureed or chunky, ready-to-serve, semi-condensed or condensedand may be served hot or cold, as a first course or as the main courseof a meal or as a between meal snack (sipped like a beverage). Soup maybe used as an ingredient for preparing other meal components and mayrange from broths (consomme) to sauces (cream or cheese-based soups).

In certain embodiments, the flavor compositions of the presentapplication are incorporated into a dehydrated and culinary foodcategory of food products, which comprises (i) cooking aid products suchas: powders, granules, pastes, concentrated liquid products, includingconcentrated bouillon, bouillon and bouillon like products in pressedcubes, tablets or powder or granulated form, which are sold separatelyas a finished product or as an ingredient within a product, sauces andrecipe mixes (regardless of technology); (ii) meal solutions productssuch as: dehydrated and freeze dried soups, including dehydrated soupmixes, dehydrated instant soups, dehydrated ready-to-cook soups,dehydrated or ambient preparations of ready-made dishes, meals andsingle serve entrees including pasta, potato and rice dishes; and (iii)meal embellishment products such as: condiments, marinades, saladdressings, salad toppings, dips, breading, batter mixes, shelf stablespreads, barbecue sauces, liquid recipe mixes, concentrates, sauces orsauce mixes, including recipe mixes for salad, sold as a finishedproduct or as an ingredient within a product, whether dehydrated, liquidor frozen.

In certain embodiments, the flavor compositions of the presentapplication are incorporated into a meat food product. In certainembodiments, meat food products include food product made by processingthe edible remains of any dead animal, including birds, fish,crustaceans, shellfish and mammals. Meat food products include, withoutlimitation, for example, prepared beef, lamb, pork, poultry or seafoodproducts. Examples of such meat food products include, for example,bologna, frankfurters, sausage, luncheon, deli slices, loaves, bacon,meatballs, fish sticks, chicken fingers, and ground meats, e.g.,meatloaf, meatballs and hamburgers. A meat food product may be combinedwith a simulated meat food product. Simulated meat food productsinclude, without limitation, for example, a meat alternative, meatanalog, soy burger, soy bologna, soy frankfurter, soy sausage, soyluncheon loaves, soy bacon and soy meatball. A simulated meat foodproduct may be combined with a meat food product.

In certain embodiments, the flavor compositions of the presentapplication are incorporated into a snack food category food product. Incertain embodiments, snack food products include any food that can be alight informal meal including, but not limited to sweet and savorysnacks and snack bars. Examples of snack food include, but are notlimited to fruit snacks, chips/crisps, extruded snacks, tortilla/cornchips, popcorn, pretzels, nuts and other sweet and savory snacks.

Examples of snack bars include, but are not limited to granola/mueslibars, breakfast bars, energy bars, fruit bars and other snack bars Incertain embodiments, the flavor compositions of the present applicationare incorporated into frozen of food products, which comprises chilledor frozen food products, for example, but not limited to, ice cream,impulse ice cream, single portion dairy ice cream, single portion waterice cream, multi-pack dairy ice cream, multi-pack water ice cream,take-home ice cream, take-home dairy ice cream, ice cream desserts, bulkice cream, take-home water ice cream, frozen yoghurt, artisanal icecream, frozen ready meals, frozen pizza, chilled pizza, frozen soup,frozen pasta, frozen processed red meat, frozen processed poultry,frozen processed fish/seafood, frozen processed vegetables, frozen meatsubstitutes, frozen potatoes, frozen bakery products and frozendesserts.

In certain embodiments, the flavor compositions of the presentapplication are incorporated into food products for animal consumption.This includes food or drinks (liquids) for consumption by agriculturalanimals, pets and zoo animals.

The presently disclosed subject matter can be used in a variety of foodproducts. The term “food product” includes any food product, forexample, those set forth in 21 CFR 101.12. Nonlimiting examples of suchfood products include frozen desserts, baked goods, fillings,nutritional drinks, beverages, salad dressing or similar dressing,sauces, icings, puddings and custards, batters, and the like. Variousbaked goods are disclosed in U.S. Pat. No. 6,536,599, the disclosure ofwhich is herein incorporated by reference in its entirety. Non-limitingexamples of bakery goods includes cookies, cakes, rolls, pastries, piedough, brownies, breads, bagels and the like. The flavor compositionsare also suitable as a component in frozen foods.

5.3 Pharmaceuticals

The flavoring compositions can also be in the form of a pharmaceutical.One nonlimiting example of a pharmaceutical form is a suspension.Pharmaceutical suspensions can be prepared by conventional compoundingmethods. Suspensions can contain adjunct materials employed informulating the suspensions of the art. The suspensions of the presentlydisclosed subject matter can comprise preservatives, buffers, suspendingagents, antifoaming agents, sweetening agents, flavoring agents,coloring or decoloring agents, solubilizers, and combinations thereof.

Flavoring agents such as those flavors well known to the skilledartisan, such as natural and artificial flavors and mints, such aspeppermint, menthol, citrus flavors such as orange and lemon, artificialvanilla, cinnamon, various fruit flavors, both individual and mixed andthe like can be utilized in amounts from about 0.01% to about 5%, andmore preferably 0.01% to about 0.5% by weight of the suspension.

The pharmaceutical suspensions of the presently disclosed subject mattercan be prepared as follows.

-   -   (A) admix the thickener with water heated from about 40° C. to        about 95° C., preferably from about 40° C. to about 70° C., to        form a dispersion if the thickener is not water soluble or a        solution if the thickener is water soluble;    -   (B) admix the sweetening agent with water to form a solution;    -   (C) admix the flavoring agent with the thickener-water admixture        to form a uniform thickener-flavoring agent;    -   (D) combine the sweetener solution with the thickener-flavoring        agent and mix until uniform; and    -   (E) admix the optional adjunct materials such as coloring        agents, flavoring agents, decolorants, solubilizers, antifoaming        agents, buffers and additional water with the mixture of        step (D) to form the suspension.

The flavoring compositions can also be in chewable form. To achieveacceptable stability and quality as well as good taste and mouth feel ina chewable formulation several considerations are important. Theseconsiderations include the amount of active substance per tablet, theflavoring agent employed, the degree of compressibility of the tabletand additional properties of the composition.

Chewable pharmaceutical candy is prepared by procedures similar to thoseused to make soft confectionery. A general discussion of the lozenge andchewable tablet forms of confectionery can be found in H. A. Liebermanand L. Lachman, Pharmaceutical Dosage Forms: Tablets Volume 1, MarcelDekker, InC, New York, N.Y. (1989) at pages 367 to 418, which disclosureis incorporated herein by reference. In a typical procedure, a boiledsugar-corn syrup blend is formed to which is added a frappe mixture. Theboiled sugar-corn syrup blend can be prepared from sugar and corn syrupblended in parts by weight ratio of about 90:10 to about 10:90. Thesugar-corn syrup blend is heated to temperatures above about 120° C. toremove water and to form a molten mass. The frappe is generally preparedfrom gelatin, egg albumin, milk proteins such as casein, and vegetableproteins such as soy protein, and the like, which is added to a gelatinsolution and rapidly mixed at ambient temperature to form an aeratedsponge like mass. The frappe is then added to the molten candy mass andmixed until homogeneous at temperatures between about 65° C. and about120° C. The flavor composition can then be added to the homogeneousmixture as the temperature is lowered to about 65° C.-95° C. whereuponadditional ingredients can then be added such as flavoring agents andcoloring agents. The formulation is further cooled and formed intopieces of desired dimensions.

In other pharmaceutical embodiments, the flavoring agent is incorporatedinto an ingestible topical vehicle which can be in the form of amouthwash, rinse, ingestible spray, suspension, dental gel, and thelike. Typical non-toxic ingestible vehicles known in the pharmaceuticalarts can be used in the presently disclosed subject matter. Thepreferred ingestible vehicles are water, ethanol, and water-ethanolmixtures. The water-ethanol mixtures are generally employed in a weightratio from about 1:1 to about 20:1, preferably from about 3:1 to about20:1, and most preferably from about 3:1 to about 10:1, respectively.The pH value of the ingestible vehicle is generally from about 4 toabout 7, and preferably from about 5 to about 6.5. An ingestible topicalvehicle having a pH value below about 4 is generally irritating to theingestible cavity and an ingestible vehicle having a pH value greaterthan about 7 generally results in an unpleasant mouth feel.

The ingestible topical flavoring agents can also contain conventionaladditives normally employed in those products. Conventional additivesinclude a fluorine providing compound, a sweetening agent, a flavoringagent, a coloring agent, a humectant, a buffer, and an emulsifier,providing the additives do not interfere with the flavoring propertiesof the composition. The coloring agents and humectants, and the amountsof these additives to be employed, set out above, can be used in theingestible topical composition.

The flavoring agents (flavors, flavorants) which can be used includethose flavors known to the skilled artisan, such as natural andartificial flavors. Suitable flavoring agents include mints, such aspeppermint, citrus flavors such as orange and lemon, artificial vanilla,cinnamon, various fruit flavors, both individual and mixed, and thelike.

The amount of flavoring agent employed in the ingestible topicalcomposition is normally a matter of preference subject to such factorsas the type of final ingestible composition, the individual flavoremployed, and the strength of flavor desired. Thus, the amount offlavoring can be varied in order to obtain the result desired in thefinal product and such variations are within the capabilities of thoseskilled in the art without the need for undue experimentation. Theflavoring agents, when used, are generally utilized in amounts that can,for example, range in amounts from about 0.05% to about 6%, by weight ofthe ingestible topical composition.

In accordance with the presently disclosed subject matter, effectiveamounts of the flavoring agents of the presently disclosed subjectmatter can be admixed with an ingestible topical vehicle to form atopical composition. These amounts are readily determined by thoseskilled in the art without the need for undue experimentation. In apreferred embodiment, the ingestible topical flavoring agents willcomprise the flavoring agent in an amount from about 0.025% to about 2%and an ingestible topical vehicle in a quantity sufficient to bring thetotal amount of composition to 100%, by weight of the ingestible topicalcomposition. In a more preferred embodiment, the ingestible topicalflavoring agents will comprise the flavoring agent in an amount fromabout 0.05% to about 1% and an ingestible topical vehicle in a quantitysufficient to bring the total amount of composition to 100%, by weightof the ingestible topical composition.

The presently disclosed subject matter extends to methods for preparingthe ingestible topical flavoring agents. In such a method, theingestible topical composition is prepared by admixing an effectiveamount of the flavoring agent of the presently disclosed subject matterand an ingestible topical vehicle. The final compositions are readilyprepared using standard methods and apparatus generally known by thoseskilled in the pharmaceutical arts. The apparatus useful in accordancewith the presently disclosed subject matter comprises mixing apparatuswell known in the pharmaceutical arts, and therefore the selection ofthe specific apparatus will be apparent to the artisan.

6. Methods of Measuring Taste and Texture Attributes

In certain embodiments of the present application, the taste and textureattributes of a food product can be modified by admixing a flavorcomposition with the food product as described herein. In certainembodiments, the attribute(s) can be enhanced or reduced by increasingor decreasing the concentration of the flavor composition admixed withthe food product. In certain embodiments, the taste or textureattributes of the modified food product can be evaluated as describedherein, and the concentration of flavor composition admixed with thefood product can be increased or decreased based on the results of theevaluation.

Taste and texture attributes can be reliably and reproducibly measuredusing sensory analysis methods known as descriptive analysis techniques.The Spectrum™ method of descriptive analysis is described in MORTENMEILGAARD, D. Sc. ET AL., SENSORY EVALUATION TECHNIQUES (3d ed. 1999).The Spectrum™ method is a custom design approach meaning that the highlytrained panelists who generate the data also develop the terminology tomeasure the attributes of interest. Further, the method uses intensityscales created to capture the intensity differences being investigated.These intensity scales are anchored to a set of well-chosen references.Using these references helps make the data universally understandableand usable over time. This ability to reproduce the results at anothertime and with another panel makes the data potentially more valuablethan analytical techniques which offer similar reproducibility but lackthe ability to fully capture the integrated sensory experiences asperceived by humans.

When conducting quantitative descriptive analysis for compounds thatmodify other compounds, the testing methodology can be adapted tocapture the change in character and intensity of the modified compound.For example, when testing for compounds that modify the saltiness ofother compounds, the panelists may first taste a salt reference ofagreed upon saltiness in order to establish a reference point forcomparison. After tasting the reference, panelists may taste and scorethe test sample for saltiness as well as any other basic taste, chemicalfeeling factor, or aromatic notes. To quantify any increase in saltperception, the panelists may then taste re-taste the reference andagain assign scores for saltiness as well as any other basic taste,chemical feeling factor, or aromatic notes. To quantify any lingeringaftertaste, panelists may re-taste the salt reference at 1 minuteintervals until their saltiness perception returns to the level of thereference. During the aftertaste evaluations, the panelists also noteand score any other basic taste, chemical feeling factor, or aromaticnotes.

7. Methods of Synthesis

In certain embodiments, the HMG glucosides of the present applicationcan be synthesized using standard chemosynthesis processes. In certainembodiments, the chemosynthesis process provides an HMG glucoside havinga purity of at least 99.999%, or at least 99%, or at least 95%, or atleast 90%, or at least 85%, or at least 80%. In certain embodiments, theHMG glucosides can be prepared using standard hydrolysis processes suchas those employing acids, enzymes, or a combination of acids andenzymes.

In certain embodiments, the HMG glucoside compositions of the presentapplication comprise one or more compounds of Formula I. Such compoundsmay, without limitation, be synthesized by any means known in the art.In certain non-limiting embodiments, compounds of Formula I can besynthesized according to the following synthesis scheme:

In certain non-limiting embodiments, compounds of Formula I can besynthesized according to the following synthesis scheme:

In certain embodiments the HMG glucosides of the present application areprepared from a food product source that is fractionated and/orextracted to form an enriched HMG glucoside composition comprising theHMG glucosides. In certain embodiments, the enriched HMG glucosidecomposition comprises the flavor composition of the present applicationand is admixed with a food product according to the methods of thepresent application. In other embodiments, the enriched HMG glucosidecomposition is combined with other compositions to form the flavorcomposition of the present application, which is then admixed with thefood product according to the methods of the present application.

In certain embodiments the HMG glucosides of the present application areprepared from a food product source that is hydrolyzed to form ahydrolysate comprising the HMG glucosides. In certain embodiments, thehydrolysate comprises the flavor composition of the present applicationand is admixed with a food product according to the methods of thepresent application. In other embodiments, the hydrolysate is combinedwith other compositions to form the flavor composition of the presentapplication, which is then admixed with the food product according tothe methods of the present application.

In certain embodiments the HMG glucosides of the present application areprepared from a food product source that is hydrolyzed and fractionatedand/or extracted to form an enriched HMG glucoside hydrolysatecomposition comprising the HMG glucosides. In certain embodiments, theenriched HMG glucoside hydrolysate composition comprises the flavorcomposition of the present application and is admixed with a foodproduct according to the methods of the present application. In otherembodiments, the enriched HMG glucoside hydrolysate composition iscombined with other compositions to form the flavor composition of thepresent application, which is then admixed with the food productaccording to the methods of the present application.

EXAMPLES

The presently disclosed subject matter will be better understood byreference to the following Examples, which are provided as exemplary ofthe invention, and not by way of limitation.

Example 1—Preparation of an HMG Glucoside Composition by Hydrolysis

The present example described the preparation of an HMG glucoside foruse in a flavor composition through the hydrolysis of cocoa bean liquormade from West African cocoa beans.

Reagents: A solution of 4N HCl was prepared by adding 100 mL 34-37% HClin a 250 mL volumetric flask and filling it with water. A solution of 4NNaOH was prepared by dissolving 80 g NaOH pellets in 500 mL of water ina volumetric flask.

Method: Cocoa liquor was run through a sieve and 30.09 g of fine powderwas weighed into a 500 mL 3-neck round-bottom flask. The liquor wasdissolved in 4N HCl (200 mL) and a stir bar was added to the flask. Thesample was stirred at room temperature until the liquor was fullydispersed and flowed freely. A condenser was affixed to the flask andheld at 8° C. A digital thermometer was pierced through a rubber stopperto measure the temperature of the solution. The third neck was pluggedwith a rubber stopper. The flask was wrapped in aluminum foil and heatedto approximately 106° C. using a heating mantle. The sample was refluxedfor 4.5 hours and left to cool to room temperature. The sample wastransferred to a 1 L beaker and neutralized to pH 7 with 4N NaOH using adigital pH meter (pH 6.98 @29° C.). The sample was divided equally into4 250 mL centrifuge tubes and centrifuged for 10 minutes @ 4500 rpm. Thesupernatant was filtered under vacuum through a Buchner funnel. Thefiltrate was then transferred to 2 32 oz plastic containers andlyophilized (yield 52.50 g).

Example 1a—Preparation of an HMG Glucoside Composition by Extraction andFractionation of a Cocoa Liquor Hydrolysate

1. Hydrolysis of Cocoa Powder

-   -   Preparation: A solution of 4N HCl was prepared by adding 100 mL        34-37% HCl in a 250 mL volumetric flask and filling it to the        line with water. A solution of 4N NaOH was prepared by        dissolving 80 g NaOH pellets in 500 mL of water in a volumetric        flask.    -   Procedure: Cocoa liquor made from Theobroma cacao cocoa beans        was run through a sieve and 30.09 g of fine powder was weighed        into a 500 mL 3-neck round-bottom flask. The liquor was        dissolved in 4N HCl (200 mL) and a stir bar was added to the        flask. The sample was stirred at room temperature until the        liquor was fully dispersed and flowed freely. A condenser was        affixed to the flask and held at 8° C. A digital thermometer was        pierced through a rubber stopper to measure the temperature of        the solution. The third neck was plugged with a rubber stopper.        The flask was wrapped in aluminum foil and heated to        approximately 106° C. using a heating mantle. The sample was        refluxed for 4.5 hours and left to cool to room temperature. The        sample was transferred to a 1 L beaker and neutralized to pH 7        with 4N NaOH using a digital pH meter (pH 6.98 @ 29° C.). The        sample was divided equally into 4 250 mL centrifuge tubes and        centrifuged for 10 minutes @ 4500 rpm. The supernatant was        filtered under vacuum through a Buchner funnel. The filtrate was        then transferred to 2 32 oz plastic containers and lyophilized.

2. Ethanol Extraction of Hydrolyzed Cocoa Powder

-   -   The hydrolyzed cocoa powder was extracted with ethanol to remove        a bulk of the salts generated during neutralization. Hydrolyzed        cocoa powder (50.36 g) was divided equally into 2 500 mL        centrifuge tubes. Ethanol (200 mL) was added slowly to each tube        as to not disturb the sample. The samples were shaken for 15        minutes on an autoshaker and then centrifuged for 10 minutes        @4500 rpm. The supernatant was decanted into a 1000 mL        round-bottom flask. The residue was scraped off the bottom of        the tubes and redissolved in ethanol (200 mL each). The samples        were shaken for 15 minutes on an autoshaker and then centrifuged        for 10 minutes @ 4500 rpm. The supernatant was combined with the        previous supernatant and evaporated under reduced pressure to        remove all organic solvent. The remaining solids were        redissolved in approximately 100 mL deionized water and        lyophilized.

3. SPE (Solid Phase Extraction) Fractionation of HCP (Hydrolysed CocoaPowder) Ethanol Extract

-   -   The extract previously obtained was further fractionated to        exhaustively remove the salts and hydrophilic molecules. HCP        ethanol extract was transferred to 14 glass vials (approximately        0.5 g each, 20 mL volume) and dissolved in DI water (10 mL). The        samples were shaken until dissolved (approximately 1 minute).        The samples were filtered through a syringe and PTFE filter to        remove particulates as necessary. A solid phase extraction (SPE)        cartridge (20 g/60 mL, C18 stationary phase) was conditioned        sequentially with DI water (100 mL), methanol (100 mL), and DI        water (100 mL). The sample (10 mL) was then loaded onto        cartridge and washed with DI water (100 mL) and extracted with        methanol (100 mL). The cartridge was reconditioned and the        remaining 13 samples were washed and extracted as previously        described. The organic solutions were combined and rotary        evaporated under reduced pressure. The residue was redissolved        in DI water and lyophilized using a Labconco freeze dryer. The        sample was separated by high-performance liquid chromatography        (HPLC) to narrow down the taste-active molecules of interest.

Example 1b—Preparation of an HMG Glucoside Composition by Extraction andFractionation of Cocoa Liquor

1. Liquid/Solid Extraction of Liquor

-   -   Cocoa Liquor made from cocoa beans sourced from Papua New Guinea        (PNG liquor) (600 g) was frozen in liquid nitrogen and ground        into a fine powder with a laboratory mill. The powder was        divided equally into six plastic centrifuge tubes (500 mL        volume). Each sample (100 g PNG liquor) was extracted with        diethyl ether (200 mL) for 15 minutes using an autoshaker to        remove the fat. After centrifugation (10 min, 4500 rpm), the        supernatant was discarded. The extraction process was repeated        three more times for a total of four times. The remaining        defatted liquor was left to air dry in a fume hood overnight.        Defatted liquor (200 g) was divided equally between four plastic        centrifuge bottles (250 mL volume). To each sample (50 g        defatted PNG liquor), 150 mL 70:30 acetone:water was added. The        bottles were placed on an autoshaker for 15 minutes. Each sample        was centrifuged (5 min, 3500 rpm) and then the supernatant was        vacuum filtered using Whatman 540 filter paper and a Buchner        funnel. The residue was freed from the bottom of the bottles by        hand and additional 70:30 acetone:water (100 mL) was added to        each sample. The samples were shaken for 15 minutes using an        auto-shaker. After centrifugation (10 min, 4500 rpm), the        supernatant was vacuum filtered again using the same procedure        described above. The supernatants from each extraction were        combined (˜800 mL) and the residue was discarded. The        supernatant was rotary evaporated under reduced pressure and the        remaining aqueous solution (˜250 mL) was transferred into a        separatory funnel (1000 mL volume). The aqueous solution was        washed with Dichloromethane (3×300 mL) to remove any xanthines.        The dichloromethane layer was discarded, then the aqueous        solution was washed sequentially with n-butyl acetate (3×300        mL), ethyl acetate (3×300 mL), and methyl acetate (3×300 mL) to        remove procyanidins. The organic layers were discarded and the        aqueous solution (F7) was rotary evaporated under reduced        pressure to remove any remaining solvent. The remaining water        solution was lyophilized using a Labconco freeze dryer (100×10³        mbar, −40° C.). Sensory analysis was performed and the savory        attribute was found to be in F7.

2. Solid Phase Extraction (SPE)

-   -   For removal of any residual salts, treated PNG liquor powder        (F7) was transferred to 14 glass vials (20 mL volume,        approximately 0.5 g sample in each vial) and dissolved in DI        water (10 mL). The samples were shaken until dissolved        (approximately 1 minute). A solid phase extraction (SPE)        cartridge (20 g/60 mL, C18 stationary phase) was conditioned        sequentially with DI water (100 mL), methanol (100 mL), and DI        water (100 mL). The vacuum was broken and the sample (10 mL) was        then loaded onto cartridge. The vacuum was resumed and the        sample was washed with DI water (100 mL). The receptacle flask        was changed and the sample was extracted with methanol (100 mL).        The cartridge was reconditioned and the remaining 13 samples        were washed and extracted as previously described. The organic        solutions were combined and rotary evaporated under reduced        pressure. The residue was redissolved in DI water and        lyophilized using a Labconco freeze dryer (100×10³ mbar, −40°        C.). Sensory analysis confirmed the presence of the savory        attribute in the organic fraction.

Example 2—Preparation of an HMG Glucoside Composition by SyntheticChemosynthesis

HMG glucosides described by the present application were preparedthrough synthetic chemosynthesis methods described in synthesis schemes1 and 2 below.

Although the presently disclosed subject matter and its advantages havebeen described in detail, it should be understood that various changes,substitutions and alterations can be made herein without departing fromthe spirit and scope of the invention as defined by the appended claims.Moreover, the scope of the present application is not intended to belimited to the particular embodiments of the process, machine,manufacture, composition of matter, means, methods and steps describedin the specification. As one of ordinary skill in the art will readilyappreciate from the disclosure of the presently disclosed subjectmatter, processes, machines, manufacture, compositions of matter, means,methods, or steps, presently existing or later to be developed thatperform substantially the same function or achieve substantially thesame result as the corresponding embodiments described herein may beutilized according to the presently disclosed subject matter.Accordingly, the appended claims are intended to include within theirscope such processes, machines, manufacture, compositions of matter,means, methods, or steps.

Patents, patent applications publications product descriptions, andprotocols are cited throughout this application the disclosures of whichare incorporated herein by reference in their entireties for allpurposes.

The invention claimed is:
 1. A chewing gum composition, comprising: a. aflavor composition; b. a water-insoluble chewable gum base essentiallyfree of water; and c. a water-soluble bulk portion; wherein the flavorcomposition comprises a flavor compound selected from the groupconsisting of:

and combinations thereof.
 2. The chewing gum composition of claim 1,wherein the flavor compound is:


3. The chewing gum composition of claim 1, wherein the flavor compoundis selected from the group consisting of:

and combinations thereof.
 4. The chewing gum composition of claim 1,wherein the flavor compound is added at a concentration of from about0.0000001% to about 1.0% in the chewable gum composition.
 5. The chewinggum composition of claim 1, wherein the flavor composition is admixedwith the chewing gum composition in an amount effective to increase ordecrease mouthfeels selected from the group consisting of a savorymouthfeel, a mouth-watering mouthfeel, a lubricating mouthfeel, aslippery mouthfeel, an astringent mouthfeel, and combinations thereof.6. The chewing gum composition of claim 1, wherein the gum basecomprises an additional component selected from the group consisting ofelastomers, elastomer solvents, plasticizers, waxes, emulsifiers,inorganic fillers, plastic polymers, and combinations thereof.
 7. Thechewing gum composition of claim 1, wherein the gum base constitutesbetween about 5% to about 95% by weight of the gum composition.
 8. Thechewing gum composition of claim 1, wherein the gum base furthercomprises a filler component selected from the group consisting ofcalcium carbonate, magnesium carbonate, talc, dicalcium phosphate, andcombinations thereof.
 9. The chewing gum composition of claim 1, whereinthe gum base further comprises a softener selected from the groupconsisting of glycerol monostearate, glycerol triacetate, andcombinations thereof.
 10. The chewing gum composition of claim 1,wherein the gum base further comprises a component selected from thegroup consisting of antioxidants, colors, emulsifiers, and combinationsthereof.
 11. The chewing gum composition of claim 1, wherein thewater-soluble portion further comprises a component selected from thegroup consisting of softeners, sweeteners, flavors, physiologicalcooling agents, and combinations thereof.
 12. The chewing gumcomposition of claim 1, wherein the flavor composition is at aconcentration of from about 0.1 to about 5,000 ppm of the chewing gumcomposition.
 13. The chewing gum composition of claim 1, wherein the gumcomposition is a sugarless gum composition.
 14. The chewing gumcomposition of claim 11, wherein the sweetener is a sugar sweetenerselected from the group consisting of sucrose, dextrose, maltose,dextrin, dried invert sugar, fructose, galactose, corn syrup solids, andthe combinations thereof.
 15. The chewing gum composition of claim 11,wherein the sweetener is a sugarless sweetener selected from the groupconsisting of sorbitol, hydrogenated isomaltulose, mannitol, xylitol,lactitol, erythritol, hydrogenated starch hydrolysate, maltitol, and thecombinations thereof.